This is one of the best ways to scale a portfolio while keeping low out-of-pocket costs.Big Picture: The Best Move for You•If you need funds now, a HELOC in your name makes sense—but keep the rental in your personal name to avoid triggering the due-on-sale clause.

This is a very personal question that is difficult to answer. 

@Levi Perl Since your single-member LLC (SMLLC) is a disregarded entity, all rental income or losses are reported directly on your personal tax return rather than at the LLC level.

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. 

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

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. 

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

People like to rent from a person not a 'brand', it's more personal.

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

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