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.

Odds are, you would come out ahead by paying to have it managed and just continuing to work. 

Odds price doesn’t escalate?  

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.

The odds are slim but the victory would be huge. 

We've thought about subbing out to a proper "property management" company but we really don't need help collecting rent or expenses (this is all done electronically online) or even finding new Tenants on the odd occasion when we have an Apt turnover (we use Brokers for that) ...

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.