Your two biggest risks are underinsurance and liabililty.I had a cabin burn to the ground a few years ago in the Gatlinburg fire. 

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.

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

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

If we have to pay for housing anyway, we might as well make the most of it.

What other boots on the ground can do inspections or meet with contractors?

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

Many people are in low rate, fixed loans so they don't have a fear that their mortgage will adjust to where they can't pay their mortgage any more.  

It can be a great option to subsidize your housing costs, gain appreciation, and benefit from someone else helping to pay down your loan.