If you're going to do it alone, make sure you your due diligence: estoppels, inspection, review, consult with a local attorney familiar with the local regulations, etc. and good luck.

Wholesalers are not regulated by Real Estate Agency, therefore not required to abide by certain laws and disclosures.

I do NOT trust “regulators”.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

As long as you listen to your insurance company's regulations as well as your local ordinances you should be fine. 

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

I'll keep you in mind if I device to pull the trigger.

As long as no “healthcare” services are provided (like medication or personal care), it’s not regulated by the Department of Health.

Hopefully this helps....You need an attorney that specializes in SEC regulations to create your PPM. 

It is right on the fringe of being legal/illegal, and lawmakers have been talking about how to regulate it for years because it can be a dangerous process that leaves end Buyers feeling like they weren't represented.....especially when they see the closing statement and find out how much the wholesaler made just by getting to the Seller first.