There are a lot of site-specific issues you need to investigate before deciding what the land is worth to you.

Fear the issues of tenant nightmares, fantastic because you won't have that with STR. 

None of these communities will be changing to residential neighborhoods, although a couple do have residential 'sides' that full time residents live in and can not be rented short term.Two of the big communities that you will have some issues with self managing are Reunion and Margaritaville.

Yes the lack of identical apples-to-apples comps has been an issue in the area for years.

The same issue happened, we would get pressured to make over 150 dials a day, yet us AQ specialists got nothing in return, and it's been nearly a year and i haven't gotten paid by either company.

@Stuart Udis I understand the importance of having the funds for repairs, vecancy and any issue that may happen.

Quote from @Jim Stanley: You should reserve insurance for large claims.Contact the city and report the issue to them.

If I had an answer to my money issue then I would quickly pull the trigger on a good deal. 

Hey @Patrick Braswell  You shouldn't have any issues getting a DSCR loan as long as you have at least 1 borrower who owns 20 to 25% of the property, or if a couple of you can get to that level combined. 

My underwriting would have this large negative cash flow for 7 years.I would do a thorough underwriting but want to show using quick math the issue so I will use the 50% rule.