This saved my skin on the exit!

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. 

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.

A purchase agreement is a waste of time and energy and complicates the issue for Harry Homeowner.This is not a beginner strategy as there are federal laws concerning approaching debtors who have been given a notice of foreclosure.

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

As lenders, well issue a prequal/preapproval letter if we've analyzed your income, assets (bank and brokerage statements to establish that you have the liquidity to afford the down payment, closing costs, and reserves), review credit of the guarantors, review the relevant experience to ensure that we're not throwing our money away on newbies that are wandering around in the dark, and have put together a reasonable plan of attack for the project.