In short, she was not truthful or accountable.

Either way I don't think anyone would be able to give you much help unless there were more info to be had.I would be extremely skeptical of someone that would say you can double your money in such a short time.

A short sale? 

If you can't, just proceed without them until you find a great one.In short, I think you have 'analysis paralysis' and think you should just start.Actually... now that I said that I do have to criticize your list a bit.First, as someone said earlier, establish what your goals are.Second, pick a market.

They did everything they could to discourage rentals short of banning them which would have cost too much to file the legal documents.

Absolutely not (Because I'm about 1.25 mil short of the 1.25 down)

I’m looking into purchasing a property in Kissimmee FL for a short term vacation rental.

This could be a good opportunity, just don't sell yourself short. 

Spending an hour with a CPA who understands your overall financial situations would be time well spent, but there are some general rules of thumb:If you hold the asset for less than one year, your profits are considered short term capital gains - which are taxed as ordinary income at your standard tax bracket rate. 

What are the bare minimum requirements I should request in a written agreement/legal document with this individual to best protect my asset in case his investment fails or falls short.