Will consider going that option. 

I think the easiest way to find the right partner is to find one that you are aligned with as far as investing in rental properties.The other option would be to keep flipping properties until you get enough money for a down payment on a rental.Another option would be to look for a BRRRR (buy, rehab, rent, refi, repeat) because then your friend could still bring money to the table and you could pay them back their portion plus interest and then you keep the rental property.What area of Chicago did you do your flip in?

Let me know if you'd like more details on this option. 

You might get quicker answers for there by reviewing some of the best STR options in your area on Airbnb and then finding the hosts or co-hosts offline to ask questions.

You could ask your accountant about options for bonus depreciation or possibly updating the properties in order to receive depreciation deductions or write-offs for repairs, maintenance, etc. 

Keep in mind there are 8,000 different lenders in the US...so, obviously we cannot speak for all of them...but the absolute best of the best lenders in this space, that have the most aggressive pricing, won't penalize you with 2 points for one option over the other.I would also question that IRS definition - that is not the case.  

There are so many caveats and unknowns here that this is just an attempt at an idea...Option 1, the four grandchildren living in the property buy out the other two:-Estimate your PITI payments based on the expected payout to the 2 grandchildren being bought out.

I've never had any issue or problems with wholesaling or assignments or options or double closes, all of which I've done.  

Someone mentioned Quickbooks, also another good option.

Solar energy is becoming a more popular option for homeowners, but it can be a costly investment that won't pay off when you come to sell.