Title company issues check to seller.

He reminded me that he had come out a month earlier and offered to help identify the leak, but my tenant told him they had already checked and didn’t find anything (an oversight on my tenant’s part).

As Jay and Jamie have stated above, a minimum of 6 different factors play into the pricing, but it is not an all or none issue. 

However, we also disabled Instant Book to avoid potential issues with one-night stays.

But usually for a tenant occupied it's like $90-120 per monthI've noticed a lot of multi-family buildings are pre-WWII housing inventory - are there restrictions or issues common with that (historic districts, crazy high utility costs, etc)?

I've also had to deal with a couple of appliance issues in a duplex I have where I do supply appliances. 

If using a lender this is a non issue.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

I'm not sure what the issue is on this.

Exterior attachments like decks and stairs are always HOA issues so I can't fathom how the driveway is not.