Not having a licensed, professional heating service examine the system and make repairs or give it a clean bill of health as necessary.It's not the tenant's responsibility to help you gather funds to fix a roof that has leaked multiple times.

You're going to want to make sure that is an expense for the seller who hired that PM (and it should be a drop in the bucket to them with the cash they're making on the sale if they didn't buy recently), not a liability of yours.This is also a good lesson on why, when you do take over the place, you either self manage, look for a manager that is willing to do a co-hosting setup where you still own the bookings, or if you do decide to go the more traditional PM route, examine the part of the contract that covers these things when choosing the manager rather than focusing on just commission and skimming over the rest. 

I'm not thankful that many people will get sick and die - that's ridiculous - but I am thankful that these times give me the opportunity to examine who I am as a man.

Then, I'd examine your goals (here's a guide to the first 4 steps you should take). 

Some of the multifamily units I'm examining seem to be from one year ago, or more.

I have exhaustively read IRC 4975 and related docs (even the IRS guidelines for auditors examining prohibited transaction violations), and I can't find anything to support what I was told by my custodian.

The old sill plates were rotting away.As for your floor joists, I don't have any experience there.I hired a structural engineer to examine and design a repair.

No higher than deal #1, but equal to it.Now let's examine the purchase. 

you need to closely examine all details.

I know people who hire others where their only job is to examine every deal possible on the MLS on a 24 hour basis.