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.

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.

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

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

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.

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.

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.

First, there a number of investment thesis' carried out by syndicators with unexpected headwinds, not solely betting on rates.  

Never been there but I bet it is nice!

Put in the effort, build relationships, prove your value, and improve your odds of finding someone to help launch you on your path.