"I feel like it's

Different areas have different metrics that decide how well they are doing.

Our opinions should not make a difference, if you're doing your diligence properly.You'll just get realtors, or real estate professionals, from both locals promoting their area based off a keyword search for posts like this.

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

Might be a little bit down the road for me, but that is for sure dream that will come true...One Chicago's best features is the lake, which I'd like more access to.

While people will share a bathroom in say a 2/1 it is likely a harder sell in a 5/2 and the price you command is less. 

Yours sounds like a much better model than most.

The migrant farm worker program works fairly well.

Once you are in the habit of not spending so much, with no debt in a few years, you will be able to save and invest like crazy!! 

It is exactly what it sounds like, buying a property that has an existing debt on it.