You are right about the risk that comes with the holding period but in my opinion sometimes you have to take the risk and make sure the profit that you generate is higher than the costs that you paid by holding the deal for a specific amount of time.

@Alex V. you've got some good responses above but this specific forum is more for residential stuff. 

@Ashish Acharya A big part of my post is highlighting how specific details in local regulations can make it increasingly challenging to operate short-term rentals, even in towns where they’re technically permitted.

While many of these issues are important considerations and should not be ignored or overlooked, there are other more crucial criteria that you must question and evaluate first.The critical risk criteria that you must review and evaluate prior to making your final decision on which 1031 Exchange Qualified Intermediary to retain includes, but is not limited to, the following areas:Technical capability of the 1031 Exchange Qualified IntermediaryInternal processes and audit controls to safeguard your 1031 Exchange funds and assetsUse of Qualified Trust Accounts or Qualified Escrow AccountsDecision criteria and guidelines for investment of your 1031 Exchange fundsProtection from potential errors or omissions by the Qualified Intermediary (E&O Insurance) Protection from potential theft or embezzlement of 1031 Exchange funds (Fidelity Bond) An experienced and professional 1031 Exchange Qualified Intermediary will understand these concerns and should be happy to discuss these crucial issues with you.

I think you have to own them if the people were nice and respectful.One thing I've found is that you have to specifically remind them in the beginning, middle, and the end, that you want to provide a 5-star stay to result in a 5-star review.

Many thanks for your consideration and input!

The cost of Spam comment made me laugh out loud; luckily that won't be an issue for me but glad to know it is available.I specifically am looking forward to reading about how you chose Teak and what the real estate/business  buying process was like.Thanks again!

But I did not want to give specific examples with no context on a location for her. 

Many who want to scale  fail to take this into consideration,  take on too many projects at once, have no capital to advance the construction and ultimately get stuck in mud unable to advance any of their projects.

Watched some You tube videos about some ways, specifically creating a property LLC with WY LLC being a member manager LLC for the property LLC.