It seems to be a comfortable level and allows me to do some work myself, which I enjoy. 

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. 

When you have a major life event (e.g. marriage, new child, divorce, etc.), the best practice is to revisit your estate planning to make sure it lines up to your current life situation. 

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

I have a tenant (hair stylist) getting close to $3k/month (plus she got the $1200 & $500 for each child) for being one of the 'stimulated' non-essential un-employed.

The state took their child away.