3) Price is too high for prospect perception of property value--- Prospects are only willing to pay so much for what a property is.

I declined to pay for the repairs.

He has someone living in the property (my grandpa's wife's daughters niece) (kind of tricky there) that only pays him at least $800 a month.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

If you gain interest on the deposit, then you must pay that interest out to the tenant each year which adds to complexity and workload.Any bank should work.

Would I be making a mistake paying the $997 for the Bnb formula?

Something that when i visit puerto Rico i have a place to stay and that will pay itself off.

They didn't pay and left the place a mess, with plenty of belongings like beds, clothes, bikes, etc. 

A couple commentors mention, pay a little more, get professional opinion.

This sounds great, but keep in mind you now must pay capital gains on that profit.