It is out of my comfort zone — I’ve never bought a house with wheels.

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. 

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).