I'm new to the real estate world but I have my other skills and knowledge that can benefit other people.

Hmm;  A landlord is forbidden to even ask about applicant/tenant medical issues, so the first problem is, How is the LL to even know of the conflict?

I typically ignore student loan and/or medical late payments.As long as they aren't delinquent a lot, can afford the place (with verifiable income), have good landlord reference(s) (aren't needy, paid on time, or paid late fees if they were late and didn't destroy the property) and don't have any evictions, then they're good.If the first guy qualifies, let him know, set up a date to get the lease signed and then mail the old guy his fee back since you didn't process it.

This a valuable skill.

I also plan to use rentals to teach my son life skills, business management, and making your money work for you.  

I'll talk to community members about donating time, either skilled (plumbers, electrician) or unskilled (help with demo).  

They aren’t under a GC either, but they are experienced and skilled.

As a newbie, this is a new skill set.

Some are entirely vacant, others not.Located in and around University Circle, close to the Cleveland Clinic, one would think that people working at CC would like to live close by, have a better than average income, thereby affording and paying higher rents.CC, by virtue of its global brand recognition and continued success in the medical field, would only attract more growth, staff and therefore -- housing demand.What am I missing here?

Find a developer partner locally who has done this a bunch, and make them an offer to partner up to bring their skill set to the table.