The tenant in place ended up showcasing some mental health struggles that made me opt out of house hacking.

@James Carlson My wife and I had the same sell/hold dilemma with our property.

One of the things we constantly discuss is benefits and health insurance.

@Steven Wilson It seems common in the NY area, especially during COVID no one wants to show a property if it's a waste of time (and potential health risk!). 

Look at the money, but look at the big picture of how real estate will/may impact your life...time, mental health, relationships, etc.

Brattleboro has a hospital as well as The Retreat, which is an in-patient hospital for mental health. 

From my perspective, if there is reasonable risk that someone's live / health is in jeopardy, like you outlined above, I'd enter.  

Also, if you decide to pursue medical school you can build a network of health care professionals which is a great resource for syndicating funds.

That said, since the value of a primary residence is a significant portion of wealth for most Americans, these price movements serve as a useful barometer of the health of the real estate market, and our economy as a whole.

While I'm trying to network with as many wholesalers and investors as I can, the dilemma is that the way to find the best deals is often to start going directly to the seller myself via direct mail, door knocking, etc especially in this market.