If the sewer line is blocked...ask the seller to have the line cleaned and allow you to re-inspect. 

Very new to the game so maybe I need to just focus my search a little better but it looks like you could walk from the Loop all the way up to Belmont Ave. and hit an open house every block!

A new huge hospital was built just blocks away, new developments with commercial buildings and gas stations around the corner, other multifamily properties have sold 500K+), duplexes have sold 300K+, and also just a few streets over there have been some higher end condos built and sold.

Inspection turned up a follow-up suggestion:  "If I were you, I'd get a drain tile test"  I asked the seller if it would be ok, they said yes, house needed new drain tile system and foundation wall re-enforcement: $15k. 

The location is on a block with majority single family homes and close to transportation.  

You might even be able to attack the expenses by doing things like metering the utilities, such as water.I believe the key to your situation may lie in knowing the rents/amenities in the immediate area (6 block radius for example) and work to position yourself well in that market.Any chance this is the 8-plex on Gumwood?

Things like AC unit fixed or windows or drain clogs.

What roles do easements, drain lines, utilities and soil samples play in determining the value?

Two blocks away there is a house for sale for $52K. 

I recently found a great SFH on 5 lots a couple of blocks from Lake Panasoffkee, which has some of the best bass fishing in the US, that I am closing on in early October.