Are there any property management companies that would be willing to actually go out to the tenants residence before renting to them (of course I would be willing to pay extra for this.)

also the company is going to allow me to be a 1099 private contractor. 

Yes, hurricanes can be worrisome, some much more than others, but with a reliable insurance policy, I have a hard time believing you will find a US beach market outside of the Gulf Coast that provides a more reliable income stream for at least 6, usually 8, months out of the year.

All these companies can do is present a product and give the financials at that time..

The cable companies require you to pay extra for something that you probably don't even want, given that they provide no value and are also another clunky device requiring wiring, space etc.

@Jeffrey L Evans Years, yes, it’s journeyman or better for 4 years; a college degree can account to 2-3 years plus 1 year journeyman or better position in a construction company.

If you are having a hard time finding one, start by looking for a local title company that is owned and founded by a lawyer. 

I'd recommend getting a free cost/benefit analysis quote from a cost seg company to determine if the tax benefits would outweigh the costs.

But if you mean questions for a GP to actually assess deals:Before I even consider signing up for a call or to be added to someone "investment club" I look up the primary partners in the company.  

This order could potentially grant you access to the property for inspection, considering the insurance requirement.If the current insurance policy is unfeasible due to access issues, explore other insurance options that can provide coverage under these circumstances.Keep a detailed record of all your attempts to conduct the inspection and any communication with the tenant, the insurance company, and legal entities.