Take the shorter loan if you’re getting the better rate and car comfortably afford it.

If your initial strategy is to house-hack in the Chicago market, you may want to consider finding a neighborhood that you are comfortable living in, and close to your job.

If I am not receiving applications within that first 7-10 days (and mind you, I follow up aggressively with the folks who attend), I'll begin dropping the price, driving larger numbers of folks to the unit, until I meet the price folks are comfortable with.Bear in mind, all of this is done with a number in mind that I am not willing to go below. 

Be totally comfortable with your decision before pulling the trigger. 

@Ty Kashmiry, also look at RentRange.If you feel comfortable analyzing properties unbiasedly, I would follow John's advise. 

They have the full strength of the Govt behind them, and they will wear you down, put you off, delay you, and make you want to eat your shoes after walking thru a cow pasture vs. deal with them.I have heard some folks says they do okay with Section 8, and that is all depends on the local director. 

The landlord would see that you actually care about the property and the prospective guests would envision themselves in a property that is comfortable and cozy.

I work in the mortgage industry and my husband is an engineer and we are blessed to both have jobs that already allow us a comfortable lifestyle and high savings rate. 

I believe that based on my experience, I'm most comfortable buying and holding, also buying properties that don't need major rehabbing (although if it's in a good neighborhood - read great appreciation opportunity - I'm open to rehabbing). 

But we're open to keeping them for now, especially in this climate (still gathering all info on tenants) Info on us: We both have comfortable day jobs, and would have emergency reserves after purchase of this property (i.e. this property won't need to feed us).