The contract is signed, the price is agreed, everyone's happy. Then due diligence starts — and that's where deals quietly die.
It's rarely one big problem. It's something random. Financing hits a snag. Two attorneys start fighting over small language. An easement nobody read carefully becomes a two-week argument. The deal was never really about the headline number; it's about whether someone clears the dozen small obstacles that show up after the contract.
A real example: two weeks of fighting, solved in thirty minutes
On one deal, two attorneys deadlocked over whether the village considered a use conforming. One wanted a letter from the village confirming it; the other argued the occupancy permit was already enough. FOIA requests went out, two weeks of back-and-forth burned, and we were staring down a missed closing.
So I drove to the village hall in person and walked out with a letter confirming the conforming use. Two weeks of attorney argument, resolved in about thirty minutes — because some things move faster in person than in writing. That's the whole job during due diligence: push through each roadblock and refuse to let any single one stall the entire transaction.
The quieter deal-killer: drift
The other thing that kills deals isn't a problem at all — it's momentum loss. If nobody's tracking the dates, the deal just languishes. People don't know the next step, the next step doesn't happen, and a live deal slowly goes cold.
I don't rely on the buyer's agent to drive it. I set the expectations and the timeline, I check in, and I make sure everyone's on track. Most of the time the buyer's agent appreciates it — they want the deal closed too, so keeping everyone moving helps both sides get paid.
What to expect in due diligence
- Financing and appraisal gaps — the lender's number or terms shift.
- Title, easement, and survey issues — encroachments and easement language are common stall points.
- Zoning and use confirmation — sometimes requiring a letter from the village.
- Environmental questions — especially on industrial and former auto/industrial sites.
- Lease verification and estoppels on leased assets — confirming the income is real and the tenants agree to the terms.
Due diligence isn't where good deals go to die. It's where good deals get managed. The difference is whether someone's actively clearing the path — or waiting and hoping it clears itself.
