I have significant concerns about mold biotoxins and health. 

Only then should you build systems around the things that are painful for you.

I'm contemplating transitioning jobs and will need health insurance while I transition.  

It is painful at first but I promise you it will pay off!"

Even though they've got the best tap on the market, first access to on-market inventory it's just tough to do there right now due to the high entry point and exactly the pain point you're facing.. the inability to cash flow with only 20% down. 

I know smaller Landlords that use Venmo but what a pain!

Or perhaps poor health or financial strain has resulted in substantial deferred maintenance, making it a difficult property to sell on the retail market--he has a problem.

I feel your pain on capital raising, 60-120k on even the most basic properties in decent areas is a huge barrier to getting started.

If I get a 3 night orphaned slot I'll lower my minimum night stay ( a pain on Airbnb, easy on Vrbo) since I can get $300 to $400 per night in the summer. 

Reason -- seller said due to health reasons they want to stay in the home until death.