I personally do not have experience managing rentals.

Are you interested in S8 because of a personal reason or you think it's the next "hot" investment idea?

I have personally owned over 200 cash flow rentals and sold them as it simply was not worth it..

I asked when the other person will retire.  

If you make the person an LLC employee you can get around it, but partner does need to be careful. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

A person files for and get's whatever from of welfare.

Personally, I wouldn't offer SubTo or a Wrap, For reasons I've written about fairly extensively. https://www.biggerpockets.com/forums/70/topics/1227199-the-m...However, I would sell on "Lease Option" and that may work for you.

Ask your employer if you can have your pay split up into three deposits, one to investments savings, one to your checking account for personal use on a daily basis, and one to an emergency account you can tap into so you don't have to tap into your investment savings.

Personally, If I could pull out a HELOC, I would use it to fix and flip which will typically make sense as you shouldnt be keeping the money out for that long and you can recycle it or pay it back and build off the capital that you got from. the flip.