@Jeff LeonardI would recommend using a broker dealerI just had a podcast with one yesterday who does exactly thisWhy do I say a broker dealer ?

If he is collecting cash payments with no lease, it's likely he's renting to the first convict or drug dealer with cash in hand.

It's like going to a car dealer and asking how much some add-on option costs and they tell that you have to buy the car FIRST, and then and only then they will tell you the cost of that add-on.

when your intent is flipping I have been a dealer for 40 years  believe me if I thought I could just hold a flip 370 days that's what I would do.. but against the rules.  

@Matthew Irish-Jones Thanks for asking!

A degenerate drug dealer.

Rental real estate is not subject to SE taxes unless (1) the taxpayer is a dealer and the property is used in the taxpayer's ordinary trade or business as a dealer, (2) the taxpayer is renting out farmland under very specific fact patterns, (3) hotel-like services are provided with the rental, or (4) the taxpayer is renting space in parking lots, warehouses, or storage units. 

The idea that someone is some brilliant wheeler-dealer because he/she bought a few rental properties and now needs to join the country club to pencil the big deals, while the peons do the dirty work, makes me laugh.I think the genesis of this mindset (I'm not saying Rosston has this mindset!)

If you are doing flipping, an LLC would be very beneficial as could have the dealer status allocated to it, and not to you personally.

If you got audited and had never made any efforts to rent it and just ran late or too long to sell, perhaps you would run into problems.I wrote about this is my blog - but here is the key part below. https://www.earlwhite.law/guide-1031-exchange-new-jersey/“Dealer Property” Not AllowedProperty held for resale (often called “dealer property”) cannot be included in a 1031 exchange.