Sounds like a win to me.

I bet a good amount of money that he never calls either.

I could write a book on how to win the lottery and its the equivalent. 

Great design, Airbnb ready, I sold it like a business that earns 2,000 monthly, a win win Lessons learned?

But I'm willing to bet that what current C4D holder is trying for, so his $ is a joke too. 

With that being said, you can build a successful STR if you win on two fronts (to simplify it)The real estate side and the hospitality side (operations).The real estate side is buying a very good deal in a market that has a history of vacation rentals in my opinion. 

Good luck in your journey . . . remember slow and steady wins the race and the ones making teh money with many of the courses being hawked are the ones selling the courses (we can attest to that as we made that mistake initially ourselves).

I completely agree with the other answers that getting someone to help you is a good bet, having someone in your corner who understands the intricacies of the tax code rather than DIYing that should save you more money (and time) than you're paying them ever since I got my first rental I've had a pro doing my taxes but kuddos to you for being able to juggle so much for so long on your own!! 

Your best bet is to take a 12-36 month STEPDOWN prepayment penalty. 

Even though I will most likely win the case with my own funds fighting it, all three insurance companies found language in the contract that disqualifies coverage for this type of event.So I dont have faith in most insurance companies - they all seem to tighten up when claims are filed.