Through market data I can't see internal or structural issues so considering the homes in this area are older that may be the culprit for the price inconsistency.

Just keep being a good landlord by making sure the property is in working order and being quick to respond to issues.  

Gary can be a good rental city, but you better have a very strong property manager or you could have major issues with rents not being paid and people tearing up your properties.  

The issue with land in general is its stark trickiness, there's no way to set a general rule of thumb as to what prices ought to be offered or what an approximate value would be, the reason?

As a tenant myself, who is just about to buy her first property...landlords who are responsive, friendly, and actually care when I have an issue make me very happy.

Sometimes building trust with Private Lenders take some time but if numbers make sense, you won't have issues having money follow. 

I was laid off 3 days after my graduation and went back to driving a transit bus and working for the computing support department with the university, the two jobs that got me through my degree.

Maybe 10 years ago or so I remember it was a pretty big issue here, when they capped real estate loans on owner occupied properties at 12%. 

@Bradley Cumming one issue with your plan is that you need "good" credit to refi!!

Good  tenants should have no issues with a M2M lease.