Potentially "flipping up" once or twice between now and then, eventually retiring to the property, or selling to acquire a retirement property there.I'm an experienced, long-time licensed agent in Atlanta and have done many fix and flip deals in the Atlanta area, but really don't have any experience with STR or MTR, especially in Fl. 

You'll also want to know what the terms of the lease you are inheriting is and decide if you are OK with that.And sometimes, it is good to just walk away and put your effort into another deal that might make you as much money for less effort.

how long to make that back? 

Hi Jacklyn, I'm a VT realtor (though I focus on northern VT), and also on the board of the VT short-term rental alliance (VTSTRA).

They are able to use the very advantageous terms and VA loan program to purchase homes that eventually become rentals properties.

It shouldn't be a problem to call and while I don't know the specific rules for Hawaii (probably something like a smoke detector in or next to every bedroom and a carbon monoxide detector in the house), rules regarding smoke detectors are not going to be "grandfathered in" (a term that building departments hate btw).

I was wondering if anyone in Georgia has worked with a good agent that has extensive knowledge of the investment market for short term rentals. 

Let me know if you would like me to get you a term sheet. 

That's the longer term plan once the last kid goes to school.

The more specific your term is the easier it will be to figure out if someone's asked it before.