Rental Property Owner & Real Estate Investor Podcast

Michigan rental property legislation is moving fast, and most of what matters to rental owners is happening in Lansing, not Washington. In this post-primary legislative update, Erika Farley of the Rental Property Owners Association of Michigan breaks down what the August primary results signal about November, which candidates are actually talking about housing, and which bills should worry Michigan rental property owners heading into lame duck and the 2027 session. Rent control, eviction expungement, junk fee rules, and a proposed cap on application fees are all in play. About Erika Farley Erika Farley is the Executive Director of the Rental Property Owners Association of Michigan, where she leads advocacy and lobbying on behalf of the state's rental property owners and housing providers. She works directly with legislators and elected officials in Lansing, tracks housing policy at the local, state, and now federal level, and oversees the association's endorsement and PAC activity. What We Cover in This Episode What the August primary results signal about turnout heading into November The Michigan U.S. Senate race and where the candidates stand on housing Why housing became a top tier campaign issue for both parties What the new federal housing law changes for HUD, Section 8, and construction The Congressional 7th race and what it signals about housing policy direction Rent control risk and why New York City is being used as a policy roadmap RPOAM's position on rent control and new restrictions on rental owners How RPOAM decides which candidates to endorse in a general election What questions go on the RPOAM candidate questionnaire The bipartisan Michigan rezoning package and who is driving it Michigan's new limit on corporate ownership of single family homes The electronic rent payment mandate tied to the state budget deal Eviction expungement legislation and the amendments RPOAM has fought for Junk fee bills and the proposal to cap application fees at $25 The tenant bill of rights package expected to return after January Why lame duck and early 2027 are the real fight for Michigan rental owners Key Insight Erika's read on why the current batch of housing bills is so small: legislators are looking for low hanging fruit they can put on campaign literature and claim they worked on housing. The bills that actually change how you operate, eviction expungement, junk fee disclosure, application fee caps, and a tenant bill of rights package, are being held for lame duck and the session that starts in January. Our words on the current activity: they are nipping at the edges. The real lift comes after the election. Why This Episode Matters If you own rental property in Michigan, the rules you operate under next year are being written right now by people who have never run a rental business. This episode tells you which bills are moving, which races decide who writes them, and where a state association can actually change an outcome. If you have been treating legislative risk as somebody else's problem, this is the episode that shows you the bill. Find Out More Website: https://www.rpoaonline.org Government Affairs and Legislation: https://www.rpoaonline.org/page/legislation Facebook: Rental Property Owners Association of Michigan https://www.facebook.com/RPOAofMichigan/ LinkedIn: Rental Property Owners Association of Michigan https://www.linkedin.com/company/rental-property-owners-association-of-michigan RPOAM in partnership with the Detroit Rental Property Owners Association (DRPOA) is hosting an in person networking event in the Detroit area on October 7. Details: https://www.detroitrpoa.org/event-details-1/detroit-rpoa-real-estate-investor-meetup-1 The Midwest Real Estate Investor Conference returns May 20–21, 2027 in Grand Rapids, MI. Details: https://www.midwestreiconference.com/ And join RPOAM in Grand Rapids for our next Government Affairs Luncheon on November 11 where we'll be taking a post-election look at what Michigan's 2026 results could mean for housing policy, regulation, and advocacy in 2027. Details: https://www.rpoaonline.org/events/EventDetails.aspx?id=2068374&group= Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com

Short-Term Rental Investing in Today's Market Short-term rental investing has changed faster than almost any other real estate strategy, and the rules that made deals work in 2021 are actively losing money in 2026. This panel was recorded live at the 2026 Midwest Real Estate Investor Conference, where moderator Jeremy Garcia sat down with three operators who have been through the regulatory grinder: commercial investor and broker Charlie Kao, Michigan short-term rental attorney Katie Johnson, and designer and vacation rental investor Sarah Doane. They cover market selection, Michigan zoning and deed restrictions, what actually separates a profitable Airbnb from one that is just getting by, and where the real opportunities sit now that the easy money is gone. About the Panel Charlie Kao is an investor, broker, and principal at Twin Oaks Capital with more than twenty years in short-term rentals and hospitality real estate. An early Airbnb adopter, he now operates across five states including Florida, Tennessee, North Carolina, and Virginia, and provides consulting, brokerage, and feasibility studies to owners and investors. Katie Johnson is a Michigan real estate attorney and founder of Katie Johnson PLC and STR Law. She advises short-term rental owners nationwide on asset protection, zoning, and compliance, and helps long-term landlords with lease drafting and risk management. She is also an active investor who owns and manages roughly eleven properties in Southwest Michigan. Sarah Glidewell is an interior designer and vacation rental investor with more than a decade of design experience. Since 2019 she has focused on designing short-term rentals built around guest experience, and she invests in rural lake and river markets in Michigan and Upstate New York alongside her husband. Jeremy Garcia moderated the panel. He operates short-term rentals and a boutique hotel in the Muskegon market. What We Cover in This Episode How to evaluate a short-term rental market when regulation is unsettled Why highly regulated markets can be safer than unregulated ones Michigan short-term rental case law and why owners are not automatically grandfathered Deed restrictions, title work, and the covenant language that shuts operators down The Park Township ban, the ongoing federal lawsuit, and what it means for other municipalities What happened when three of four short-term rentals were shut down by regulation Using 1031 exchanges to move out of markets that turn hostile Whether the short-term rental market is actually oversaturated How to read AirDNA data without drawing the wrong conclusion Rising costs, shrinking margins, and the shift in Airbnb guest fees Bringing cleaning in-house and what it does to cleaning cost per turn Using AI for guest messaging and after-hours support Guest avatar selection and how it drives every design decision Which amenities actually produce return, including hot tub revenue data Hedging seasonality with year-round amenities in cold weather markets Short-term rental tax strategy, depreciation, and offsetting outside income The luxury design gap that most operators are ignoring Working with municipalities: grassroots campaigns, local counsel, and goodwill with neighbors The biggest mistakes each panelist made and what they cost Key Insight Sarah Glidewell and her husband had four fully operational short-term rentals in Michigan when the state pushed regulation down to the local level. Over two years, three of the four were shut down. They 1031 exchanged all of them into new properties, and every one sold for over asking price within the first week on the market. They did not lose money. They lost time, and they lost the compounding. Her takeaway: she now buys nothing without legal review first, and she deliberately targets markets that are already regulated. Why This Episode Matters If you are underwriting a short-term rental in an unregulated market because it looks like open runway, this panel gives you the case law and the operator experience explaining why that assumption can cost you the asset. It also gives you a concrete answer on saturation, on which amenities produce measurable revenue lift, and on what a professionalized short-term rental operation actually looks like now that mom-and-pop listings no longer compete. Find Out More Charlie Kao Website: twinoakscap.com LinkedIn: linkedin.com/in/charliekao Instagram: @charlesckao YouTube: Twin Oaks Capital Katie Johnson Websites: strlaw.com and katiejohnsonplc.com Podcast: STR Law Instagram Sarah Glidewell Instagram Jeremy Garcia Website: bookdreamstay.com Midwest Real Estate Investor Conference This panel was recorded live at the 2026 Midwest Real Estate Investor Conference. The 2027 conference is scheduled for May 20 and 21, 2027. If you want a full two days of sessions like this one, plus direct access to the operators, investors and attorneys actually doing this work in the Midwest, put it on your calendar now. Details and registration at midwestreiconference.com. Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com

Most real estate investors spend decades building their portfolios. Very few have a plan for what happens when it's time to step back. Whether the goal is passing assets to family, bringing in a successor, or simply having choices later in life, succession is rarely just a financial question. The relationship dynamics, unspoken assumptions, and fear of hard conversations are what cause most transitions to fail. In this episode, Elizabeth Ledoux, founder of The Transition Strategists, breaks down why only about a third of businesses successfully transition to the next generation, what the other two-thirds get wrong, and how to build a transition roadmap that actually works for real estate investors and family business owners. About Elizabeth Ledoux Elizabeth Ledoux is the founder of The Transition Strategists and creator of the Transition 3.0 methodology. She has spent more than 30 years helping family and private business owners navigate succession, with a focus on the relationship challenges that cause most transitions to fail. Her firm's Evolve program has helped clients achieve a succession success rate of over 90%, compared to a national average of roughly 33%. Elizabeth began her career as a petroleum engineer before founding multiple businesses and moving into strategy consulting. She is co-author of three books including the award-winning "It's a Journey: The MUST-HAVE Roadmap to Successful Succession Planning," and host of the Business Transition Roadmap podcast. What We Cover in This Episode Why investors default to lawyers and CPAs first and what they miss by doing so Transition 1.0: building a secret succession plan that no one knows about until the owner dies Transition 2.0: telling people what will happen, but still top-down with no co-creation Transition 3.0: building the roadmap together, with the transitioner always as the driver Why strategies fail when people are not engaged: "Strategies don't work when people don't execute" The fear that keeps owners silent: what happens when you tell people you are thinking about leaving Why outside facilitators unlock conversations that families cannot have on their own The real reason a son said he wanted a job in the family business, and what he actually wanted A real estate disaster: how an undisclosed will nearly destroyed a mother-son relationship, required three separate valuations, and generated enormous legal bills A real estate success: how one developer's family divided a hotel, spa, senior living, and development portfolio equally among three children and built a functioning board together Why "people don't live up to your expectations, they only live up to their commitments" The Evolve program: a 12-month flat-rate roadmap process and what it covers When to start: why earlier is better and how Elizabeth ran her own succession roadmap years before she found her successor The hub model: how The Transition Strategists coordinates with your existing CPA and attorney without replacing them How to set up a board for a family-owned real estate business and why it is a practice, not just a structure What the 73-year-old single-family portfolio owner should do first Key Insight Elizabeth described a father who believed he had everything handled. His son was running the operating company. The will was prepared. In his mind, it was all set. When he died unexpectedly, his wife, who had never been involved in the business, took over out of fear. She was the primary owner and had no context for what the plan was supposed to be. The son had to sue his own mother to preserve the business. He won, and was able to buy her out. But the cost was three separate valuations at roughly $20,000 each, significant legal fees, and a family relationship that took years to partially repair. The father thought he was protecting everyone. What he was actually doing was protecting himself from a difficult conversation. Why This Episode Matters Real estate investors pour years into building portfolios but most have no transition plan that accounts for the human side. The legal and tax structures can be perfectly designed and still fail if the people involved have not agreed to their roles or do not understand the plan. Investors with family members, partners, or staff who will inherit, buy in, or step up need to start this process well before it is urgent. This episode gives a clear framework for doing that, with real examples from real estate families who got it right and families who did not. Find Out More Website: https://www.transitionstrategists.com Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits. https://www.rcbassociatesllc.com

Self-storage is one of the most misunderstood asset classes in commercial real estate. Most investors assume it's a simple, low-complexity play. Ryan Gibson built it into a billion-dollar operation by treating it like anything but. As Co-Founder and President of Spartan Investment Group, Ryan has organized over $1 billion in capital across 90 facilities and 7 million square feet in 15 states, ranking Spartan as the 29th largest self-storage operator in the country. In this episode, he breaks down the market selection framework, operational systems, and ancillary revenue strategies that separate serious operators from everyone else in the space. About Ryan Gibson Ryan Gibson is Co-Founder and President of Spartan Investment Group, the 29th largest self-storage operator in the United States. He has organized over $1 billion in capital across 90 facilities and 7 million square feet in 15 states. Before real estate, Ryan was a commercial airline pilot. He applies aviation's checklist-driven, risk-first discipline to every aspect of how Spartan evaluates deals and operates properties. He is also co-host of the Passive Income Pilots podcast. What We Cover in This Episode How aviation checklists and go/no-go decision-making translate directly to real estate underwriting The Swiss cheese model of risk stacking and why deals fail for multiple reasons, never just one How to identify the right moment to set the parking brake and walk away from a deal Why Ryan avoids hyped markets and what he looks for in lesser-known markets instead Specific markets with strong fundamentals: Lincoln NE, Northwest Arkansas, coastal South Carolina, coastal Georgia, and markets near military bases and universities The market structure insight that led Ryan to self-storage: 70% mom-and-pop ownership, 10% REIT, and the aggregation opportunity in between How renting his own storage unit during a home renovation changed Ryan's entire investment focus The fish-in-the-middle strategy: buying mom-and-pops, aggregating, and positioning for an eventual institutional exit Spartan's current portfolio (90 stores, $1B AUM) and growth target of 300 stores The virtual manager kiosk system: how one store manager can run five facilities remotely How Spartan's distributed team opens East Coast and West Coast stores outside normal office hours AI voice technology running the after-hours call center, and why it performs as well as their former offshore team How 65% of bookings happen through the kiosk screen with less than 10% face-to-face The tenant insurance captive: how Spartan adds $70,000 to $80,000 in NOI on property takeover, worth over $1 million in valuation at a six cap Why U-Haul partnerships are no longer worth the labor cost How to register every property for cell phone tower placement and generate triple-net lease income Leverage thresholds by deal type and why fixed-rate debt is non-negotiable How Ryan uses Claude AI connected to Spartan's data warehouse to cut 50 monthly investor updates from 80 hours to 7 hours Key Insight Ryan discovered self-storage the way most people discover something that changes everything: by accident. He was renting a unit during a home renovation that stretched from five months to a year and a half. When the landlord raised his rent 20%, he tracked the owner down to complain. The owner told him he had 500 units, raised rents 20% after six months, and nobody ever moved out. Ryan did the math on the spot. That one conversation reoriented his entire investment career. Today Spartan owns 90 facilities. It started with a $20 monthly bump on a unit full of stuff he probably should have thrown away. Why This Episode Matters Self-storage is often treated as a set-it-and-forget-it asset, but Ryan's framework shows it rewards operators who understand demand dynamics, leverage discipline, and operational integration at scale. Investors considering the asset class will come away with specific market criteria, a concrete underwriting framework, and a realistic picture of how scale changes the economics. The tenant insurance captive alone is a revenue strategy most real estate investors have never encountered and can apply immediately on their next acquisition. Find Out More Website: https://spartan-investors.com LinkedIn: https://www.linkedin.com/in/ryan-gibson1/ YouTube: https://www.youtube.com/@passiveincomepilots/videos YouTube: https://www.youtube.com/@SpartanInvestmentGroup Facebook: https://www.facebook.com/spartaninvestmentgroup/ Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits. https://www.rcbassociatesllc.com

Most real estate investors evaluate deals. Ben Kahle evaluates the people running them. As CEO and Managing Partner of Wellings Capital, a private equity firm with more than $500 million in assets under management, Ben has spent 11 years building a rigorous operator due diligence process that puts people above property. In this episode, he breaks down how Wellings vets commercial real estate sponsors, what their 28-step due diligence process actually looks for, and where investors consistently misjudge risk by focusing on the asset instead of the operator behind it. About Ben Kahle Ben Kahle is the CEO and Managing Partner of Wellings Capital, a private equity firm with more than $500 million in assets under management and over $225 million in investor equity across 1,100+ investors. He joined the firm as a $12-an-hour intern in 2015, became a partner in 2019, and now leads the company's investment strategy and operator due diligence process. Wellings invests as a joint venture equity provider in multifamily, mobile home parks, self-storage, and industrial assets, with a minimum check size of $4 to $5 million per deal. What We Cover in This Episode Why Wellings Capital thinks of itself as a people business, not a real estate business The core investing principle: a great operator in a mediocre market beats a mediocre operator in a great market How Wellings uses a 28-step due diligence process to evaluate commercial real estate sponsors What incentive structures for onsite managers and asset managers reveal about operator quality Why track record analysis requires cycle context, not just raw performance numbers How Wellings verifies operator financial strength using personal financial statements, tax returns, and Trepp Why Wellings shifted from LP investing to joint venture equity provider three years ago The control rights Wellings negotiates: forced sales, manager removal, and CapEx draw control The 80/20 (or 90/10) reality of deal and sponsor quality in today's market The "death by Google" screening method for surfacing sponsor red flags fast The cockroach test: why one visible problem usually means more you cannot see Third-party resources for investor due diligence: Invest Clearly, 506 Group, Private Investor Club How Ben's team is using AI to analyze deals and run due diligence workflows Key Insight Ben Kahle draws a line most investors never make explicit: he would rather put capital into a mediocre deal in a mediocre market with a great operator than into an outstanding property with a mediocre one. That conviction runs all the way down to the onsite property manager's bonus structure. Wellings wants to see incentives tied directly to NOI, occupancy, and collections before they commit a dollar. After reviewing more than 1,100 deals in a single year, Ben says operator quality is the variable that explains most of the outcomes, good and bad. Why This Episode Matters If you are placing capital with a sponsor or evaluating any deal led by someone else, this episode gives you a concrete framework for what to look for and what to walk away from. Ben covers the process, the red flags, and the specific tools he uses in plain terms that any investor can apply regardless of check size. Find Out More Website: https://www.wellingscapital.com Free resources on mobile home parks and self-storage: https://www.wellingscapital.com/resources Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com