However, with my 1 short term rental I am struggling to remain confident that this is the right strategy as when something does happen it seems I lose at least a couple days with them dispatching and then following up.  

Not to mention, the property was probably mismanaged by an “out of continent” investor who just had a terrible experience losing Haiti during the Haitian revolution.From a real estate perspective, the Louisiana Purchase was a game-changer.

It is a strategy for not losing it. 

Even with an LLC and PUP, you still lose the property.

Will probably lose the deal because of their lack of response and poor service. 

There are calculators online but make sure you are familiar because I get a lot of people call me because their loan officer failed to run the numbers and they are getting ready to lose a deal or earnest money.If you want to go FHA you can always put more down but I would take a look at Fannie Mae as well for High Balance areas.  

Does the agent care as much about Buyer B losing their earnest money as Buyer A?

If you lose, you may then also responsible for their legal fees.

I know people with huge door counts who lose money every month.

I wanted to learn and if it were to go bad id rather lose my own cash than be upside down in a bank loan.