Not sure if this appeals to youJoint Ventures: Partnering with a larger hospitality group or another investor might not only bring in funding but also expertise and industry connections. 40% of a deal is better than no deal.

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

Now, you can get some wholesalers but they usually don't know if the property will fit the requirements and regulations but you can learn that from the Realtor. 

As with most municipalities and jurisdictions, the evolution of the AirBnB market has spawned regulation and restrictions on where, when and how a STR can operate.

If I had the business headquartered at some commercial or industrial space, I could deduct the entire cost of the space. 

There are often local Facebook groups for specific strategies 

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

Looking great! 

Zach, specifically, does not demonstrate himself as an excellent businessman.

Remember your situation is unique so it's important to consult with a tax advisor or CPA to explore all available options and ensure compliance with tax regulations.