I had a 3000sf house near Houston that needed a roof. Bids were in the vicinity of $18-20k. Shingles.
I have a 3200sf house near St. Louis that is getting a new roof through insurance. Existing roof was @ 2years old and insurance paid us a check for $18K. This will sound weird, but they paid exactly how much it's going to cost their recommended roofer to fix it.
What a great opportunity to get into a multi family. If the repairs scare you, walk. I think you mentioned all 4 doors bring in $2700 rent (have you verified that via bank statements and not rent roll?). Supposing you spent, wildly, that it cost $250k all up to fix. I don't mind those two numbers at all, I think you are still making money.
I know some here are nixing the idea and wanting the best deal they can find so turn their nose up at it. Well, they're the ones that miss this deal.
For me, at the end of the day, if it's making me money each month, I want in. Someone else is paying your note, the place is appreciating, and you'll have another form of 401K. Don't be scared of it. But only you hold all the info on this transaction. I would not hesitate. PM me the address, maybe I'll take it off your hands.