Then there’s city regulations—some places heavily restrict short-term rentals, so you’ve got to check the rules.If you find the right spot and automate stuff (guest communication, cleaning, etc.), it can be profitable.

I partnered with an experienced STR agent, Troy Nowak, and purchased my first short-term rental in Palm Harbor at the height of the real estate frenzy, navigating fierce competition and ultimately overcoming What made you interested in investing in this type of deal?

Best thing you can do is do some research to find a seasoned real estate agent in your area or use Bigger Pockets to ask other members who they had sucess in using. 

The right agent will provide a pro forma breakdown on every property they look at, have repair costs estimated, CapEx, etc...

One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

Those agents have their ego at the expense of the relationship, and there are such agents actively participating in this thread.

Well, we get here and his agent is telling my agent it will be another month for another court date that will allow him to sell the property.

Based on what my real estate agent thinks that this quote will be, roughly, and the after repair value, it looks like I could buy this property in cash, spend a month or two fixing the damage, and then put a mortgage for roughly 1.6x what I paid for it and thus have a cash flowing property at a few hundred dollars per month and a little more money in my bank account ready for a down payment on the next deal.

The real estate agent doesn’t pay for problems.

Guests cover the cleaning cost.