We are fighting but I wanted to throw this out there.

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.

I'm hoping to branch out into additional investment properties but the $1k/month that I'm seemingly throwing away makes this difficult.I thank you all in advance for your thoughts and feedback.

If  a property throws off 30k NOI but I have to be involved and be there multiple times a week then it's a job.

Just to throw some numbers out there,  If it costs about 45K to rehab and rental income should be about $24000 a year.

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.  

I throw my listings on my wife’s fb marketplace instead of mine.

The rate is variable, and you could really move the needle on debt paydown if you throw a ton of that cashflow at the loan.