I'd advise you to stay away from an asset that is extremely distressed and in need of a ton of repairs. 

He started out as a highway patrol officer, but after our second child was born we both decided it was best for him to quit and be the stay at home parent and for me to keep working.

The glue tabs Depot have do not stay together.

My long term tenant/friend (at this point) moved with us and stayed until our second boy was born.My wife and I both work, so I'm looking for a little more hands off approach. 

I plan to thoroughly vet each association, but there's only so much that you can do to ensure they stay on track.- Use restrictions and potential profits during the busy season may prohibit us from getting the best use out of the place.- Appreciation will likely be better on the beach.

So he will be frequently in the new place but when it is rented out with airbnb he will stay at his other apt. 

For example, I work with one lender who will offer 75% LTV on the purchase price (NOTE : sometimes hard money lenders will require first time investors to stay at 70% LTV) plus 100% rehab so long as the total LTV does not exceed 90% of the purchase price. 

How long do you plan on staying or holding onto the unit? 

Beyond that, the economics of how you hit your expectations stay the same.Again, I hope you get a few answers on performance on here.  

When I go to the Keys, I stay in Key Largo because its about halfway between Miami and Key West. key Largo itself isn't that impressive in my opinion, I just like the location.