To set the stage, I'm owner of a short-term rental property in the Poconos in PA and we use a property management company for bookings, maintenance/cleaning, guest management, etc.This past weekend we had a guest booking but when the guests arrived Friday evening the house had no running water, though it had been running fine earlier in the day when the Property manager (PM) was at the house to give a final check and leave the welcome packet.

I am an agent and own a short term rental mgmnt company so am very familiar with the STR rules and regulations as well as the best areas for that strategy locally. 

Does anyone have suggested property management companies they've used in Florida that they can recommend I reach out to, to see if we're a good fit for each other?

It looks like this particular investor preferred the low level price point and the risks that come along with it even though he was buying from a company who could offer him both types of investments on the complete opposite side of the risk spectrum.

Of course it is very important to do proper due diligence on the investment and the operator.As far as self-directed IRA there are number of companies offering such service, this topic has been discussed here on the forum many times so you should search using this keyword and learn from those discussions.

My current property management company doesn’t offer this service, and the only company I know of is very hard to communicate with.

Hard money and private investing are both ways to finance flips, but they work a little differently.Hard money loans are typically from companies or private lenders that specialize in short-term, high-interest loans.

I personally believe his contract job contract got cancelled as i know others from his company left that same week. 

I have tried to get quotes for these properties and I haven't found a company that is willing to insure me because I have open claims.

Kyler, call your a couple of insurance companies and get a formal quote so you can take this back to the seller.