In other words the government gave you a 30k loan from your taxes at 0% interest that you have to now pay back. 

I know that much of it is based on personal risk tolerance but any advice would be greatly appreciated. 

OBX is a great place, but it will take a very long time to be cash positive based on its current pricing, management fees and the short season.We were going to also use it during offseason but its just a pain to get too.

My wife's even planning to camp out there for a couple of weeks to make sure things get done right as we are based out of NJ, so time's of the essence.

They may be able to give you some input and feedback based on their experience. 

That is, these returns are projections, based on our analyses and best guesses, but they aren’t guaranteed, and there’s always risk associated with any investment.

Everyone has opinions but some are not based in reality.If you are not providing significant services, like daily cleaning, on site chef for meals, custom tours etc. you should be filing on a schedule E. https://theshorttermshop.com/is-short-term-rental-schedule-e...

The targeted distributions with DSTs are based on the original investment amount.

In other words, if the S Corp is the right route for you, you will have to form either an LLC or a C Corp and elect to have it taxed as an S Corp.

That's the conundrum and game-on for you.