I would personally keep the property unless it's going to be tough to cover the difference. 

Personally I am not sure what investing out of state looks like, and I would truly feel incredulous if I could get help from any of you amazing friends here on bigger pockets!

Driving pilings, sea wall retention systems, special sewer containment systems, home security, building quality, stainless steel fixtures for salt, etc.  

You need to pass "material participation" test and personal use test, but that's for your future tax professional to explain.Yes, bonus depreciation is possible, but only on the current value of the personal property and land improvements.

I would highly recommend staying away from anything being transferred from one person to the other directly.

If you are doing this for your personal properties, I would consider Quickbooks or Stessa.

I would personally wait to buy a property until you're down there.

My current rentals are all in my personal name with conventional loans.

But I began this reply with IF, because if they are all cash-flow positive, I would personally not seek to pay any of them off early (depending on your age), and instead save that money to put towards obtaining additional properties.

It's about being a person great mentors want to help!