And, as I understand it, even if you hold for 12 months, the IRS will consider what your planned exit strategy was, and if they determine that you had planned to flip it the whole time (and never rented it), you'd be considered a "Dealer" for that property, and would still owe ordinary income on the business income (regardless of the 12 month hold time).

The better deals will be had by buying from homeowners who've upgraded vs the slew of used dealers who post on Craigslist.

Being shady is just not good business in my book and I hate to hear stories from people who have been victims of shady dealers. 

All is well @Matthew Irish-Jones, just moved out to Chicago, Illinois, so it’s been a new chapter, but I already see property management in my future haha!

Having been a senior portfolio manager for fixed income broker dealer overseeing all of our whole loans, I can tell you for sure it is indeed looked at.  

You locate two dealers who have the car, dealership A & B.

I personally have 1 LLC for multiple properties and maintain good liability coverage and strong business practices (don't rent to drug dealers and murderers, keep buildings in great shape, etc.)

wouldn't hurt to separate DEALER property like the flips from the INVESTOR buy and holds for IRS audit purposes. 

Your best bet is to contact MH Dealers and RE Brokers in the area you're interested in investing in.

I also contacted antique dealers to increase the income on some of the furniture.