Your best bet would likely be to wait until you are surely moving and then look for a two-family to house hack in that area.

Zoning issues are out of my league but bet you know how to make it happen with your expertise!

The prime defense that we used to hedge our bets was to ensure that any property we looked at would be able to function as a long term rental.

Everything. 2) Make sure you have a signed contract that is legal and thorough. 3) keep the progress payments relatively equal to the work being done....example - don't pay for tile when you're still doing framing.Go get some bids and then come back and talk to us again... 

if you do, simply don’t bet the farm doing so.

My worst-case scenario is I buy an in-progress rehab all cash in a few months.

Your best bet from what you said, for proximity and ease of use and volume of vacationers would like be in the Woodstock area or the Catskills.

I speed-read it all but I'd bet most people won't...2) I need interest rates to go down right now so I can buy a couple of rentals.

Sure, but it's a pretty long shot bet.

There's not a lot of online tutorial for setting up QBO in real estate industry so your best bet is to hire professional to set up the books and the process and teach you how to use it.