In your opinion, is it on the horizon where the county passes some form of STR regulation which impacts all cities?

Philips, Winter Garden, Horizon West, and Celebration. 

What most forget about JV's due to their focus on raising capital, flexibility, or broadening your investment horizon is that it is a partnership and if you think Real Estate investing my be stressful at times throw a few inexperienced partners in along with money they are looking at and having to work together as well as manage emotions and you have a perfect storm.The point I am trying to make is the successful JV's I see are comprised of experienced investors who have opened their financials to each other, as well as background checks or any other verification of finances and more importantly character to have a comfort level with one another.

Also note that the national builders would be more likely to buy an option on your parcel if you give them a longer horizon.

I also believe there is capital value increase on the horizon.

Possibly invest into a syndication with a short time horizon or some debt.

The issue I am having is that every deal i have analyzed so far looks to be terrible in terms on CoC ROI, monthly cashflow ( -7% to -10%) and also Annualized overall return ( negative in short term and < 10% over 20 year horizon).

There's also a chance the property depreciates in value over the time horizon.

So my buyers 5 to 10 years of owning horizon looked completely different than the sellers numbers.

What I was always told is to always remember how hyper local real estate is, a beautiful property physically and financially can be crushed if the neighborhood isn't hospitable and doesn't seem to have a horizon for improvement in sight.