Long term strategy is to hold until it makes sense to sell, and that might be after only 2 years so I can reap the benefits without getting killed in taxes.

Eg if owning a house for the mortgage, insurance and taxes alone would cost you over $3000 a month (mortgage alone on a 25 year amortization for $500K is $3000 a month, goes down to $2700 on a 30 yr mortgage). 

Enter recurring charges and automatic late fees.

In my state that would be an expensive change as I would be paying state transfer tax on the move along with other costs plus I would need to consider whether I wanted to buy title insurance on the property for the new LLC.

After he was successful in being more profitable than his neighbours (one thing he's done well with is driving traffic to his direct booking sites to cut out the host sites that take so much in fees) he started taking on investors that put the 20% down for say a DSCR loan.

It would be best to speak to a seasoned cpa to address your tax concerns. 

For probably 90% of the people it does not provide anonymity, it doesn't protect you from liability, and it doesn't save you any taxes. 

He teaches on how to be a wholesaler of notes, where you find a seller and a buyer, and you just charge a small 1-6% fee of the note size.

https://www.biggerpockets.com/...BiggerPockets has a tax pro resource page.

Use the more conservative numbers.That is a huge HOA expense.HOA fees can go up and rules can change so be warned.