Jig,

There is a saying with cars 'buy what you will be using the car for 90% of the time" anything else rent per occasion.

I'm not from Chicago or lived in the US of A before but being in Toronto, Canada in the 'burbs and just being in Canada alone I know about snow. Been here my whole life. I love and welcome snow/cold temps more before I don't like heat but that's just me. My dad bought a 1998 Ford Escort Z2X (I think si the model number) manual transmission before back around 2000 and 8yrs later it's driving still good given it's ~100,000+ km. Just regular maintance and brake job. I don't have children myself but have been around people with kids before helping them out and with a 4yr old most cars will do as you don't really need a large size car as the kid is still small. If the child is ~10-12yrs old then a mid-size car would give a little better room.

How much do you know about emergency car kits and tire change/battery boosting? We have a Jeep Grand Cherokee here which is new so I keep my car kit well maintained but on the used Escort I put a bit more preparation in the emergency kit as the car is second owner and also the battery has a bit of sulphering on it.

I hope you know how to change your tires, boost a car battery, and how to boost a car battery via a emergency batterypack. I'm going out for my night ride right now but I'll drop some links afterwards which I have put on my ipod just for those 'oh-crap' moments if I needed to fix/brush up on something if it did happen to me.