Hey @Trevor McCormick (and @Fab Ragh) - as many have stated, Kissimmee and the Orlando market in general are extremely competitive.

I'm no expert, but do know for a fact that you are much more likely to find "good deals" off MLS – through mailing, cold calling, off market groups/connections, etc.

First you have to face the local municipalities & will be extremely difficult to get the zoning approved. 

DOM nationwide isn't really terribly useful; in extreme situations we will already know the national economic situation.

Cold, drafty, and couldn't keep the mice out.The thing rented like crazy.

And end of year actuals never pencil out like the spreadsheet...I'm not saying that it's a bad idea; I would just urge you to proceed with extreme caution.

I use it for my rental property extremely easy to use.

.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

I tell them the story of my neighbor whose pipes burst on the 3rd floor during a bad cold snap. 

I'm extremely new when it come to real estate.