EP 476 - The Five-Year Reality Check Every Investor Needs

Jan 27, 2026

38:24

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What did you think of todays show??

Profitable one year, underwater the next — real estate doesn't always math the way you expect. In this episode, Mike shares why short-term numbers lie and what his once cash-flowing rental portfolio looks like five years in. You'll hear why “looking good on paper” can still turn into a cash problem, what most people misunderstand about tax incentives and lending rules, and how you can avoid surprise tax bills.

Topics discussed:

Introduction (00:00)

Your five-year portfolio reality check (01:13)

What people misunderstand about real estate tax incentives (04:00)

Why you need to stay on top of professionals you hire (09:53)

Why Dylan is replacing his acquisitions manager (13:30)

How your problems evolve as you scale (20:28)

Lending rules that catch investors off guard (23:05)

The truth about private mortgage insurance (28:51)

What investors miss about DSCR rates and loan structure (31:02)

Early takeaways from 2026 (35:37)

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