@Jacob Dalton - I have been a landlord in Chicago for 13 years and as an investor agent I have worked with 200+ investors on the north side of Chicago over the last 10 years. 

In my experience, the best thing to do is warn people over and over again.

It seems there is a great discrepancy over whether it is smarter to stay local or not for your first rental investment. 

These guys did this for over 20 years .. it was determined that they actually made less than 12 loans in the whole time bringing in Millions of dollars 10k at a time to small of an amount to sue over..

Despite my concerns, I allowed the appraisal to proceed.

Typically those purchasing cash aren't inspecting every home, they're walking it or having their go to GC walk it and already know what they see that may be a concern. 

If you have any concerns, you may also discuss alternative payment options with your tenant.

They seemed good, and looks like they have prior experience managing the building I’m buying (based off the leases that were submitted to me) but way to expensive to what I’m use to … $137 - $184 per door (over 10%) and then $750 per door for the maintenance reserve. 

I'd be happy to make connections over similar goals, and to learn about tax info for DC, great spots to buy, and trends for rentals.

Perhaps valid concerns.