What criteria would you be looking for in order to qualify and what are the chances of pulling this off? 

When you find out the present zoning of the property, the future land use and the local agencies comprehensive plan for how they see the area being developed (all can be done at the local planning office) you will have a much better idea of what you have just bought.If the land could in any way be developed into something more than single family residential lots, i.e. if there is any multi-family or commercial component than I would advise you to hire someone qualified to help you with the site planning of the development.

"Income Charge- This charge may only be levied by the Board in accordance with the Community Authority Declaration.

No and you need to put this on hold and research the condo nuke that's about to hit Florida in the form of new legislation that no longer allows condo boards to defer necessary repairs. 

The first phase or about half the lots will be short term gains with the possibility that the second phase may qualify as long term gains.

I highly recommend a well-qualified REALTOR who works with investors and knows how to help you best.7.

I chatted with a lender about the DSCR loans and he said that Padsplit (room shares) would not technically qualify for DSCR although if it’s vacant at the time of closing, it should be fine.

Loose deck board or stair etc.

Personally, I'd be nervous to not get some type of deposit from my guest because I like for them to have "skin in the game" 

Short term, assuming the real estate lobby doesn't sue this to keep delaying/appealing, once it goes into effect there will be no more broker fees paid by tenant *unless they hire the broker*Some long term effects I can predict already: - Landlords now having to absorb broker fees will bake this into the rent (e.g. how "no fee" units typically are priced a little higher than other units) - Real estate board will require another document (or checkbox) for tenants to sign stating that they're hiring the listing broker and responsible for compensating them for their fee *if* they apply and are approved- Regular New Yorkers will have an even harder time to find an apartment because you cannot legislate/regulate away a housing crises...