Cheap is not always good.

Relate to them based on where they might be traveling from, suggest a local hike/restaurant/attraction you like. 

I don't necessarily have the time for a reno/flip and I'm constantly travelling.

The property is a cheap 4-plex in a college town near us that is already fully rented, and the rental income surpasses the PITI, but that’s where we run into my question.

Example a cheap home that rents for 1000 might work well but your analysis from above would be a good bit different. 

Yes, the midwest is cheap yet compared to most of the country.

You can buy something like a cheap Arlo camera system at Costco and pay for the Internet connection in one of your units.You could ask law enforcement to do routine drive-bys or safety checks.

Most importantly, is this worth not only $800.00, but is it worth my time to travel to this conference?

I'm a travel nurse and have been sending applications via email.  

I'm in Bridgeport now because I wanted a yard and cheap parking :) There's always something to do and somewhere to eat around in River North.