I've never heard of a Work Comp waiver - it's possible it exists in some states.If you have a person who would normally be defined as your employee for Work Comp purposes and they get seriously maimed on your project site I'm betting that waiver isn't worth the paper it's printed on.

Looking at Airbnb/Vrbo (30+ day stays), Furnished Finder, and even scanning Zillow and Facebook group for comps is likely going to be your best bet.

I bet that electric bill will be HIGH with that put in.

I tell all my clients how important it is to buy with vacant units.If you only have $100K and living for free is an absolute must, then your best bet is to look in markets like Birmingham (I own a triplex there) or others in similar price points.

And you are right, it is a big risk betting on the appreciation.Our strategy to wait to buy the bigger house originated from the multiple factors (interest rates, inflated prices, no need for moving just for elementary school and unstable professional life).

They bet on the Jockey more than the Horse. 

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.

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.