Odds are you will lose your EMD if you back out, which may be a better option than sticking with this deal (depending on the amount and how it impacts you financially.)

Yes, they don't have as many restrictions in terms of Attorney's needed and silly laws but, If you can conquer wholesaling here? 

Also be mindful of existing or proposed restrictions - I don't recall anything extreme proposed in Ludlow or Dover, but Wilmington is being very aggressive in all but eliminating STRs.

You can end up in an odd spot where these previously disallowed losses are disallowed nearly permanently until either a) you are no longer a real estate professional and you un-aggregate your rentals or b) every single one of your rental activities is disposed of.I have one client right now with some material passive activity loss carryforwards, that the decision was made to wait to make the REPS related election until they utilize these loss carryforwards, so they don't become trapped. 

It may be, may, but odd's are time will come that selling to redeploy will be called for to retain the classification ranking at time of entry. 

HOAs can also put restrictions on rentals such as the percent of rentals vs. owner occupied.  

One they fought hard and took it to the state AG for privacy, which should have no pricy restrictions on it anyway. 

I'm also not interested in condos/townhouses as I owned one previously locally, and it really restricted what I could do. 

Nashville, IN is known to have rental restrictions on STRs in the area, so I would double check the regulations.

But you have to weigh all the factors to gauge your odds.