DiscoverRetire Sooner with Wes MossSocial Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics
Social Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics

Social Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics

Update: 2025-08-28
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Discover how money choices today can influence your financial confidence and retirement happiness in this engaging episode of the Retire Sooner Podcast with Wes Moss and Christa DiBiase. Gain perspective on retirement planning strategies, Social Security rules, tax considerations, and investing trends that could shape your financial journey.


• Examine how large IRA withdrawals—such as those used for home renovations—can affect Medicare premiums, and consider strategies to help manage taxable income.


• Break down the concept of tokenization in investing as Robinhood and the SEC highlight this trend, and think about the possibilities for fractional ownership in the future of investing.


• Weigh the trade-offs between applying rental income toward your mortgage principal versus investing it for long-term retirement flexibility.


• Clarify how Social Security survivor benefits may extend to grandchildren, what dependency rules apply, and why guardianship status alone may not be enough.


• Review why withdrawal planning and tax awareness—including the value of professional guidance—remain key components of effective financial planning for retirement.


• Learn how capital gains tax brackets work and why timing investment sales can play a role in overall tax outcomes, especially for families with changing incomes.


• Assess the role of REITs (Real Estate Investment Trusts) within a diversified investment approach and what to weigh when considering them as part of your retirement income plan.


• Explore the growing use of artificial intelligence in financial planning, from investment research to estate modeling, while keeping in mind its potential benefits and current limits.


Stay informed, stay engaged, and stay confident in your path forward. Listen and subscribe to the Retire Sooner Podcast for thoughtful conversations that support a fulfilling retirement journey.



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Social Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics

Social Security, Taxes, REITs, and More: Exploring Key Retirement Planning Topics

Wes Moss