Personally, I'd go with the As-Is scenario.

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

There is realized gains & profits, and UN-realized gains and profits.

Have the tenants take and send pictures of any maintenance items and video chat with the repair person as needed.If you ever get in a situation where you just feel like you can't do it or don't want to do it, you can always put a PM in place at any time. 

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

Personally I would pass but if you go forward I would do a lot of research on the group you are renting to and get a very large security deposit to cover damage. 

Personally, I just don’t know if it’s worth it.   

Be prepared to follow up multiple times, using different forms of communication—calls, emails, and if possible, in-person visits to their office.

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

Tell me - someone selling their home to your son, Subject-To - is this a person who has made good life choices?