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.

Probably about five or more life insurance brokers that specialize in cash value policies are active on BP reach out to them to get some other options and feedback.  

Buy 4 more properties - one approximately every 3 months, based on the following logic = always fill existing property with a tenant prior to moving on (I'm new, and this is my way of managing risk); build resources to purchase next property (I have pretty decent purchasing power right now through conventional lending with my current job, and I also have a private lender ready to loan on my next property, and I also get a quarterly commission check that provides a nice financial bump every 3 months); finding a property takes time, but it is worth it to find the right property in the neighborhoods I want to invest in, at the right price.

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. 

So, the tenant has the power to give you 30 day notice and leave as well. 

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.