Both the UIC area university village, bridgeport, Pilsen, and U of C area Hyde Park, kenwood and Bronzeville are rapidly rising due to the expected things being built around them

Few rise to high levels of success. 

Never take anyone else's ARV calculation for face value, especially people who have something to gain from an inflated ARV.

You can find the details here:https://www.biggerpockets.com/forums/55/topics/692382-from-bankruptcy-to-1-000-units-part-2-rising-from-the-ruins

It seems to me that if your father-in-law is as big of a fish as you say, then he is testing you to see if you rise to the challenge and are worthy of the empire he's built or if you cower from an unbelievable opportunity because of a perceived short-term gain of only $1200 per month.What type of properties are these?

https://www.wlky.com/article/louisville-residents-will-soon-see-property-taxes-rise/28622227I'm actually okay with this.

So this property would need to sell for $175000 or rents would have to rise to $2300 per month.

It could just be that they don't like companies outside of their city buying properties, renovating them and selling them to investors at what they think are inflated prices.  

I am a rising college senior and plan to take a year or two between undergrad and the start of medical school.

This number will likely only go up over time as rents rise and your interest cost reduces as your loan is being paid off.