Additionally, I am aware that once I move out, I can list the home on VRBO and several other platforms to help boost bookings.The reason why I'm considering/leaning toward selling the house, is that when I begin to run the numbers, the expenses exceed what I could potentially make.

It's been rezoned to allow a live/work component, allows 4 units, and the FAR allows room for plenty of additional SF. 

Not saying it can't work... just requires additional caution.  

I’m in no rush to move once I get into something, especially if it makes more sense to stay out for an additional year or so.

This week mortgage applications hit a low not seen since 1995.One result: mortgage industry employment is down 20%.

As OP said, hard to find umbrella that will cover STR papered insurance unless I find a carrier that writes it under my name personally and names the LLC as an additional insured (I own my properties under LLCs).  

Aim to purchase and renovate a property for resale, with the ultimate goal of acquiring additional income-generating rentals.

Additionally, so far the economy has shown pretty strong resilience, with historically low unemployment rates.

For example when a large employer in a small town closes up shop taxes may continue to go up at the same time as people move away or can't afford rent forcing rents downward.

The buyer can decide how to use the additional space.