Since then I've begun to use the rent collection portion as well, which removes yet another layer of complexity!

My $10k example was admittedly unrealistic.However, by way of further background, @Dustin Heiner wrote an excellent article on this topic on his website masterpassiveincome.com titled "What to Do When A Buyer Backs Out From An Assignment Of Contract".In it he suggests a scenario where the assignee decides not to proceed, perhaps after discovering a big ticket repair item that would cost significantly more than the portion of the assignment fee held in escrow. 

I like the idea of multi family properties, this is something we could occupy one portion of, however these are uncommon in the city we live.

If you rent longer than 30 days, you’ll skip a large portion of the taxes and fees levied on STRs. 

Time will tell how many a "significant portion" is exactly, as they seeks to turn around the struggling business.

And several I talk with will cover a large portion of the closing costs.

Are you saving a portion of your monthly rental income for capex, vacancy, and repairs?

Of that $4K, she only gets part of that, she has to pay a portion of that to the company she works for.

A portion of it to reserve for refinancing and most of it to pay off credit cards and prior debt.

Try to focus on the time, and effort portion of the decision.