I am trying to figure out what is more desired and which would have a better resale and rent value... either a walk in shower or a shower tub combo? 

Tenants have no desire to maintain a 1 acre property so you're going to be stuck paying for that.

ONe thing to consider is flip the tables.. become the bank.. let those that have the stomach and desire to landlord do that work.. you just collect checks each month your still invested in the exact same asset but with none of the liablities and day to day interface with PM and tenant.. 

I’m looking at duplex in a very desirable neighborhood, where I want to live, close to a ton of amenities.

During the GR we converted the less desirable unit back to LTR rental during the school year.  

How would you respond to application where the desired move in date is Oct 1 but we discussed Mid Sept?

This is a highly desired area with great schools and above average income levels.

Currently it’s in semi-desirable area about an hour outside the main metro area.

Citing that piece of true information gives no information about the desirability or value of Chicago's real estate.To even make any generalized statement like "Chicago is undervalued" is ridiculous.

The Auto Shop Owner (Buyer) tore down the SFH and now has one large 18,000+ sf commercial corner lot in a desirable neighborhood in Houston.