Police are a hammer and to them everything situation is a nail. 

that said it's very unusual to nail down a place that will cash flow here, the more common scenario here is a significant chunk of your mortgage. 

@Christian Latimer nailed it with Facebook market and Nextdoor!

I think you need to nail down the potential upside in rents for the 8 plex, as well as quantifying any added value you can capture by raising the NOI.

If you check the area where the leak seems you may find it is due to something simple such as a "popped nail" (if a shingle roof). 

I would want to nail that down with Estoppel certs and walk if it turns out the seller is trying to dump his problem in your lap.

To quote carpet you really should just have someone price it and charge that amount.As for holes, in my state nail holes are normal wear and tear, whereas anchors for heavier items like TVs are not.

Erik W Nailed it.

@Chris Shue@Dan Portka nailed it with that list. 

(I do moderately stupid daily so I am less concerned about that.)Thanks, AndrewYou hit the nail on the head, avoid doing anything "outstandingly stupid".