We wanted to eventually use this land for short and long term rentals and it would take much money and time to make that happen.

If you bank your timeshare (I use RCI) or there is  Interval International, two of the largest ones)  then you can reserve a timeshare at a more popular, in demand location.  

As I bounce around from one idea to the next, I was wondering if anyone in the community has been successful with starting up a short term business in the Dominican Republic?

Hey Orlando,Long story short - no. 

The return on investment just doesn't make sense sometimes in the short term.

I would rather buy a solid piece of real estate and realize the rent potential in the short term future than just buy something for cash flow sakes."

Looking to use the short term rental loophole.If I use the short term rental loophole for my STR, I material participate and do a cost seg study.Can I take the value of the building in the first year as depreciation and write it off against my wife's income?

While there are certainly no vacationers here, there are a good amount of people that use short-term rentals for contract work for 1-3 months.

Is it short term or long term rental?

You regretted getting into this 2 years later, you'll regret selling these properties shortly if they are in good areas of Durham.Fast solutions have slow problems.