About this episode
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
