While I have looked into remote rentals ( I was an assistant property manager for roughly 3 years) I don't think it will be something that much harder than the craziness I encountered at work.

However, I am asking for advice on the situation I have encountered. 

And/or someone would have to do a LOT of scamming for it to be worth it at $500 a pop.Because it's so small, small enough that it looks like an appraisal fee and/or "confirm you aren't wasting my time" fee (rather than being a large "I'm trying to scam you" non-fee), and if there's an online presence indicating folks have done business with them and/or you know people that have, I'm going to say you're probably safe in this case.

The advantage to the medium-term rental is that you are probably not going to encounter laws/HOA rules that limit them (HOA can be tricky, so double check), they are less work than an STR, the money is still better than a traditional rental and the demand is relatively high if you are close to a college or a hospital or something with appeal that needs employees. 

Handyman charges outrageous prices and gives the girl at the PM office a couple hundred bucks for helping him with the scam. 

The major issue you will encounter will be cost due to historical restrictions.

Of course you will make mistakes and encounter ups and downs, but if you are diligent and work through the rough patches you will be successful!

It is far easier to qualify for each property as you encounter them.

I do have a few follow-up questions if you don't mind me asking: Were there any insurance premium implications that you encountered because of the bathroom's toilet type?

How to prevent such scams?