My Question regarding AirBnb when a home is USDA:I am planning on buying a home, using USDA, and am looking for one where I can easily create an Airbnb space.

Some of your statements just don't add up to an agent not performing as you expected, actually helping you win a bid in an obviously competitive market where you'd lost several already.

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 have a few thoughts.1) You don’t have to invest where you live so I think your first move is to pick an area where you will be happy.2) I still like FL although insurance is a problem and the rental and STR market has softened.

That was when, as many recall, interest rates where on the rise.

There are some instances where investors had to sell their properties since the whole neighborhood went to the city and made it illegal to do it. 

No one on this forum will be able to answer his question unless he wants to provide his income tax information.Capital gains at the federal level is either 0%, 15% or 20%.He may have capital gain carryoversIt may potentially be considered a business and subject to ordinary income which would be at his marginal tax rates.No one knows where the flip is done or in what state which impacts his state income exposure.

A small benefit could be the quads being purchased with traditional residential lending where as the 16 unit would require commercial lending.  

This is where a simple, old school paper application/word document will serve you well. 

If so, where/how did you find distressed and motivated sellers that were willing to do those deals?