You should have this lined up and understand the options before you commit yourself to anything Especially if you are using hard money or any other then your own cash.

Will consider going that option. 

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

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. 

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.

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.

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.

Next time you check out Houston, you can take a wide look at Katy, Cypress cause 99% of investors stick to those lower-entry points but take a look at Spring branch, Meyerland, airline heights, montrose, memorial park and don't fall victim to people pushing 3rd/5th ward.Austin has a lot of really good neighborhoods, but none are as great as say River Oaks or Piney Point.