What the listing app doesn't show you

Question

Pulled a CT tax deed property last month. Strong ZIP, sellers market, comps going pending in a week. Back taxes under $2,000. Looked like a discounted house.

Then I pulled the assessor card.

It's not a house. Vacant lot, under a tenth of an acre, town-assessed at $500. The recorded owner lives in the house next door. I was about to bid on somebody's side yard. An automated rent tool had quoted me $2,700 a month on a structure that doesn't exist.

Fifteen years in mortgage underwriting taught me to read the record before the listing. At auction, three things decide the outcome and no app shows them cleanly: what is physically on the parcel, which liens survive the sale, and what the redemption window does to your capital.

Here's a live one. I pulled the current CT auction list this morning and cross-checked it against my own records from three weeks ago. Eight properties are gone. In this state, a property leaves the auction list when the owner pays in full or files bankruptcy. Eight redemptions or filings in under a month, and nobody publishes that number.

What's the one diligence step that has saved you from a bad raise of the hand?

Simone Owens · Answer

@Bill B. That’s exactly the trap. An automated tool quoted me $2,700 a month in rent on a vacant lot, and a newbie who trusts that number walks in and bids up a strip of grass. The AVM confidence is the danger, not the help.

The difference is who’s reading the record. A model guessing from comps is how people overpay. Pulling the assessor card and the lien history by hand is how you catch that it’s a side yard with a possible federal lien. I don’t trust the tool’s number, I verify the county’s. Fifteen years in underwriting taught me the machine flags, the human decides.

Curious whether you’ve seen the AI-overpay problem show up at the auctions you watch, or if it’s still mostly the seasoned bidders in the room.

Bill B. · Answer

This is one of the flood of “outcomes” we’re going to have from AI. Two different out of state or newbies are going to listen to their AI and bid the sucker up. The “loser” may never know lucky he was.

Simone Owens · Answer

@Ned Carey You're right, and the $500 flag is exactly why I closed the app. The drive-by is the gold standard, no argument. My angle is what happens before the drive-by, when you're screening 40 properties across six towns and can't visit them all. The assessor card and lien check tell me which ones are worth the trip. It thins the list so the windshield time goes where it counts. Curious how you triage when the auction list is long and spread out.

Do you drive everything, or cut it down on paper first?

Ned Carey · Answer

The property assessed at $500 should have been a clue. I drive by 99% of everything I bid on.