You might want to consider other options, like teaming up with a reliable friend or family member, to navigate this situation.Getting advice from experienced professionals in the real estate industry can offer valuable perspectives and assistance in dealing with legal and ethical issues.

Who knows.Another option would be to buy a small parcel and slowly build a house with/for him and pull owner permits.Am I nuts?

Now you may be able to find options with less points, but the only way you may be able to avoid those is by going with a DSCR option. 

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.  

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.