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© Michigan Short Term Rentals
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Learn to navigate the nuances of short term rentals in the state of Michigan. On the podcast we talk about:
- Vacation rental regulations
- Tools for optimizing your rental
- Systems and processes for operating your short term rental
- How to find a profitable vacation rental area
- Amenities for vacation rentals
We also interview owners of some of the best vacation rentals in the state of Michigan and beyond.
- Vacation rental regulations
- Tools for optimizing your rental
- Systems and processes for operating your short term rental
- How to find a profitable vacation rental area
- Amenities for vacation rentals
We also interview owners of some of the best vacation rentals in the state of Michigan and beyond.
183 Episodes
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Most operators are doing the math wrong. Tony and Jordan break down five principles that turn ordinary investments into something that compounds in ways most people never see coming and why in this business, one plus one almost never has to equal two.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedInKatie Johnson https://www.katiejohnsonplc.com
Kenny Bedwell is back. This time he breaks down what the data is actually showing in the STR market right now, why the top 10% of hosts keep pulling further ahead, and how his nearly year-long New Orleans hotel renovation has been a crash course in patience and permitting. We dig into which markets are flying under the radar, how to think about boutique hotel and micro resort opportunities, and why regulations might be the best thing that ever happened to serious operators.https://www.strinsights.comFollow Kenny on InstagramFollow Kenny on Facebook https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
IV Beaton spent years helping grow Life House, one of the fastest-growing hotel management companies in North America, before carving out its software unit to launch DIAMO. In this episode, he breaks down why small independent hotel owners are finally in a position to compete with the big brands and why switching from short-term rental pricing logic to hotel pricing logic is harder than most people expect. Tony also shares his own early results using DIAMO at The Windmoor Lodge, including nightly rates jumping 30 to 40% after making the switch.https://www.diamo.aiIV Beaton's email: iv@diamo.aihttps://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Most investors are competing for the same deals on the same platforms. Tony and Jordan share the simple principle that's been opening doors nobody else even knew to knock on and why it might be the most overlooked edge in the entire game.staythewarren.comhttps://www.facebook.com/StayTheWarrenhttps://www.instagram.com/staythewarren/https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan break down their first cash-out refinance on a 5-unit property they took from $60K in gross income to $220K+. That property just appraised at $1.2M. They share exactly what they're doing with the equity, why a pool could add $75K in annual revenue, and when leveraging equity is a smart move versus a dangerous one.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan unpack how cost segregation can dramatically reduce taxes for short term rental owners.A cost seg study breaks out components like driveways, pools, cabinets, appliances, landscaping, and sheds into shorter timelines. That allows you to front load depreciation into year one.In one example, about $130,000 was accelerated. For a high income earner in a 25% bracket, that could mean $30,000 to $40,000 in tax savings immediately.Key points:• You must materially participate to use losses against active income. Track your hours.• Portable structures not permanently affixed may qualify for 100% write off in year one. Some may not even require a formal cost seg study.• Seller financing with little or no money at risk can cap or eliminate your deduction. The takeaway. Cost seg is powerful, but only if your deal structure supports it.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
This episode is a naming playbook for boutique hospitality. Tony and Jordan walk through five naming considerations that directly impact bookings and brand momentum. They share real examples from The Windmoor Lodge and their current Bridgman project, including why some “good” names fail when you search them, map them, or try to match them to the guest avatar you actually want. They close by reinforcing the bigger point.........you are selling an experience, and the right name helps the design team, the community, and future guests feel that experience before they ever arrive.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
This episode breaks down why most people stall even when they know what to do. Emanuele explains mindset as the beliefs shaping how you see yourself and life. They cover imposter syndrome, language traps like “I’ll try,” and why clean decisions plus long term commitment create real change. Growth starts internally, then shows up externally.Follow Emanuele Pani on Instagramhttps://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Katie Johnson is back with a real update from the front lines of Michigan STR law. We talk Park Township’s ongoing battle, why “we’ve always allowed it” is not the same as “you’re protected,” and what happens when a township flips the switch after investors have already poured six figures into a property. Katie also breaks down the legal reality behind deed restrictions, permit caps, and why more Michigan municipalities are using old ordinances to shut down STRs today.STR Law Podcast https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
This episode is a behind the curtain look at what it actually takes to make a small motel feel like a high performing group retreat. They talk big group bookings pushing ADR way up, the operational reality of rural markets, and why bigger assets can actually be easier when they support dedicated staff. They also hit the “do it right the first time” principle, including examples like plumbing, aging heating units, and finding efficiency rebates that can materially offset upgrades.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Hiring is the bottleneck most STR operators refuse to admit. In this episode, Tony and Jordan break down why growth stalls when the owner is still doing “busy work” and taking every guest problem personally. They unpack the hire that doubled their business, the mindset shift from job to real business, and a simple way to think about ROI on employees. The punchline: stop asking “how do I do this better” and start asking “who can own this so I can grow.”https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Most investors focus on price and projections. Experienced operators focus on financing structure. In this episode, Tony and Jordan unpack two lending products that are changing how they and their clients approach vacation rentals and boutique hospitality.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
The 2026 Michigan STR Conference is officially live, and this episode explains why this year is different.Tony and Jordan unpack what happens when you get in the right room, around the right people, at the right moment. They share how proximity to high-level operators, investors, and thinkers has directly led to deals, partnerships, clarity, and faster execution in their own journey.This episode is an invitation. Not just to attend a conference, but to step into a bigger table, sharper conversations, and a higher standard heading into 2026.https://michiganstrconference.comJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan unpack a mindset shift that changes everything: you are not the same person you were when you failed last time. They use an Indiana football clip as a punchy example and apply it to business, fitness, and investing. The core idea is simple. Most people make decisions using a “mechanical mind” that treats past outcomes like permanent limits. But your skills, network, confidence, and experience have evolved, which means your current version deserves a fresh attempt. They also hit a real limiter that shows up when you start using other people’s money: stewardship. You hesitate because you care, but that same care is what eventually builds trust, track record, and the right to play bigger.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan break down a counterintuitive idea: the most interesting person in the room usually is not the loudest or the funniest. It’s the one who listens, asks elite questions, and makes other people feel seen. They talk about how to avoid shallow conversation starters, how to build real connection even when you don’t share interests, and why stories beat facts every time. They also hit the power of becoming a connector and how relationships compound when you consistently add value without being transactional.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
This is a candid year-in-review episode focused less on wins and more on evolution. Tony and Jordan unpack the moments that forced them to grow: larger projects, higher stakes, constant problems, and the realization that the next level requires different people, systems, and discipline. They talk openly about calm under pressure, thinking bigger, investing in health, and why the right team matters more than perfect timing.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Inside this episode, Tony and Jordan unpack their annual strategy retreat and reveal the three levers that are shaping their next five years of growth. They share why hiring earlier creates the breakthrough, how long-term thinking beats short-term perfection, and how stewardship builds the relational capital needed to scale. It’s a candid look at the decisions, discipline, and mindset shifts driving consistent growth. Grass Lake Lodge Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan break down how their investor journey evolved from doing a first flip with a close friend to bringing new investors into every deals. They talk through what actually attracts capital in real estate deals proof of action, reputation, conferences, and showing your work in public so money starts coming to you instead of you chasing it.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
Tony and Jordan walk through their newest deal under contract a twenty four unit motel in Southwest Michigan that they have been tracking for years. They break down why they kept coming back to this specific property, how they underwrote it using real comps instead of the seller’s weak performance, and why they are convinced the market can support boutique level rates once they add design and amenities. Along the way they share candid lessons from earlier multi family and motel projects and what finally gave them conviction to pull the trigger on a larger asset.Join the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
This episode breaks down the real-world shift Airbnb made to an AI-driven review removal system and how hosts can get negative review removed within the new system. Tony shares the exact framework he used to get two unfair reviews removed in under 90 minutes after weeks of failed attempts. Jordan adds insight on why strong systems, clear guest expectations, and consistent communication make these appeals stick. If you’ve ever felt powerless dealing with retaliatory or irrelevant reviews, this one gives you a roadmap to take control again.Sean Rakidzich YouTube VideoJoin the Michigan Short Term Rentals Facebook groupConnect on Instagram Subscribe on YouTube Connect with Tony on LinkedIn Connect with Jordan on LinkedIn
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