Why No One in Your Real Estate Deal Is Protecting Your Money

By Mike DeHaan, Dan Austin, Dylan Koch · September 28, 2026

Every closing involves a cast of professionals: an agent, a lender, a title officer, an insurance agent, a CPA. On episode 503 of Collecting Keys, Mike DeHaan, Dan Austin and Dylan Koch argue none of them are paid to protect your dollars, and that assuming otherwise is how investors quietly bleed money. Here's what they've caught, and where they've cut costs.

Why are the incentives in a real estate transaction stacked against the buyer?

Dylan recently helped close friends buy a primary residence, something he says he'd only do for people he's close to. The house had been listed at $600,000 for two weeks and was vacant. County records showed the sellers had already bought another place, so they were carrying two mortgages, and Dylan knew there were no other offers. They offered $50,000 under list. The listing agent said the offer was insulting. They went under contract $40,000 below asking.

Mike's read: that listing agent just watched her commission shrink on a lower sale price, and she isn't alone. The buyer's lender earns less on a smaller loan, and the insurance agent writes a smaller policy. Dylan admitted that if he were acting as a general agent instead of a friend, he probably would have pushed his clients to offer more. As Mike puts it, everyone in the chain is aligned against the buyer's interest at the same time.

Do you really have to check your CPA, title company and attorney?

Dylan's summary of the off-market business is that it's professional babysitting: title companies, contractors, sellers, loan officers. He said four out of the last five HUDs he reviewed, on both the buy and sell side, came back wrong by thousands of dollars.

Mike shared his own example. While reviewing his returns for a personal loan, he found his CPA had left an entire income source off his 2024 taxes, roughly $30,000 worth. He ended up paying about $7,800 the following year, plus penalty interest, because he'd signed without reading it. Attorneys are no different in his experience: send a lawsuit over with no instructions and you may get a bill for research you never asked for.

• Read the HUD line by line before wiring or signing
• Read the return before you sign it, not after
• Tell counsel exactly what you want done and why

Why do the numbers you project rarely survive to closing?

Dylan described a deal set up as one of the biggest spreads he's ever had in his market, until the seller's payoff statement came back almost equal to his resale price. The seller hadn't paid since 2024, and a secretary forbearance loan sat on top of the mortgage balance. What looked like a large check turned into a few thousand dollars.

Mike pointed out that sellers in that spot often refuse to move forward once they see the number, even though daily penalty interest and fees mean waiting a few more weeks can leave them with nothing. Dan's take is that most distressed sellers got there through indecision rather than one bad decision: liens, unpaid contractors, foreclosure, all compounding from things they didn't handle.

Small surprises land too. On another closing, Dylan got a call the morning he was clear to close about a mechanics lien filed the previous Friday. He negotiated it down to about half, got it released, and still closed with owner's title insurance.

How can you cut recurring costs on a rental portfolio?

Mike reshopped insurance across his personal portfolio and dropped his total annual bill by more than $3,000. His view is that the claim experience is unlikely to be great regardless of carrier, so he'd rather pay less. Dan's point: if you do file, you tend to pay it back through premiums anyway.

Mike also got a refinance appraisal on a triplex that came in about $150,000 below the county's assessed value. He submitted the appraisal to the county expecting a fight and got an email the next day saying they'd make the adjustment, worth close to $1,000 a year.

The same logic applies to any recurring bill. After repeated internet outages, Mike called and got a $203 credit, roughly three months of service. He figures this work takes thirty or forty minutes, and if you won't do it, a VA can sit on hold for you. Dylan raised the flip side: his primary appreciated so much after buying in 2020 that the insured amount fell below value, so he needs it raised, not lowered.

How do you plan taxes and still stay lendable?

Dylan said half of his last CPA conversation was about the tension between keeping AGI high enough to qualify for a primary residence loan and not overpaying in taxes. His lender said a standard thirty-year loan would be difficult given everything he has going on and floated a 5/1 ARM with a 25-year amortization instead. Dylan raised his own W-2 salary to make the picture cleaner. Dan's point: underwriters want consistency over several years, not big swings, even if the swings add up to more money overall.

Dylan also noted, citing his CPA, that the married-filing-jointly rate jumps from 24% to 32% around $403,550, and that sheltering $100,000 of income as a real estate professional can take roughly a million dollars of property. Mike overpaid his 2025 estimates by about $106,000 and plans to apply it forward. On investors who claim they never pay taxes at high incomes, Mike's opinion is blunt: they're either lying or haven't been caught yet.

The through-line of episode 503 is that nobody in the transaction is checking your math for you. Listen to the full episode for the rest, including the hosts' debate on paying cash for a primary and borrowing against it.

Taxes, Legal & InsuranceRentals & Cash Flow

Educational content from the Collecting Keys podcast. Not financial, legal or tax advice.