At some point, every real estate investor has to ask a hard question: Is this property still working for me, or am I just holding it out of habit?

In this episode, Dan Ihara, a national real estate planner with more than 400 completed 1031 exchanges and over $110M in deferred capital gains, joins Brian Hamrick to talk about how investors should evaluate aging properties, declining returns, and next-stage portfolio decisions.

Dan specializes in helping investors recognize when an asset has quietly stopped performing and how tools like Delaware Statutory Trusts (DSTs) can be used to transition into truly passive, tax-efficient ownership—without emotional or rushed decisions.

What we cover:

How to tell when a property has become dead capital
Why many long-held assets produce 0–2% cap rates without owners realizing it
How rising taxes, insurance, and expenses quietly erode returns
Why most investors don't actually know their current cap rate
The difference between appreciation and real performance
How DSTs work in practice as a 1031 replacement property
Who DSTs are designed for—and who they are not
Passive income vs active ownership late in an investor's career
How step-up in basis can eliminate capital gains for heirs
The role of 721 UPREIT conversions and long-term planning
Why real estate causes family conflict after death
How pre-inheritance planning can prevent disputes
Why real estate planning is about clarity, not control

This episode is especially relevant for investors who are:

Over 50 and thinking about simplification
Tired of active management but hesitant to sell
Concerned about capital gains taxes
Focused on wealth preservation and family harmony, not just growth

Resources Mentioned:

Book: Property Decisions: Avoiding Family Disputes and Painful Taxes to Create a Legacy That Lasts by Dan Ihara
Available on Amazon (ebook and paperback)

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