To get something in your price range that is in a more-desireable area for you and your family to live in, maybe check to see if you can get a fixer upper funded with private (or hard) money, then once it is "move-in ready" refinance with the VA loan that is available to you as a vet. 

Many if they fail right out of the gate have no desire to continue ( IE that did not work) and or lost money and can't continue no matter what they desire.

I don't think the numbers look that spectacular: First, anything that rents at near $100/ft in the Midwest needs to be in a very desirable location or a top quality property (complete rehab) and have amenities (2 BA's and a garage...you only have one bath).

There is lots of opportunity there, especially in older desirable neighborhoods.

Passive income is the only way to go to help you build a real estate empire (if that is what you desire).  

I have a business management degree and desire a real estate license as well.  

If they highly leverage their investments and/or have a very high desired rate of return - what they pass on maybe very appealing to you. 

Just a few thoughts from me:- If you are in such a desirable neighborhood and you've owned the property for 11 years, why is it not cashflowing?

I think this is a great deal needing minimal work in an area that is very desirable!

Time is a good strategy IMHO- maybe have him call you in a few months if he still hasn't gotten a desirable offer?