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*leighbird4**
I'm a Chicago nestie, and I saw your posts on raising a family in a city and wanted to comment but I was afraid you woudn't see it, so I'm finding you here. Hope that's okay.
I'm a life-long city of Chicago resident and my mom has had epilepsy since before I was born. My father was a city cop so we were required to live in the city, and now as an adult I wouldn't have it any other way. I feel that in many ways my life has been enriched by city living, city schools, and just the overall experience.
As far as my mom...well, my mom had her first seizure at 17. She hasn't driven since then and had to rely on rides from my dad or from friends, or on the bus and her feet in order to run simple errands or to get to church or get her hair done. Living in the city really helped her be as independent as possible because if Chicago didn't have a reliable transit system she would have been pretty much homebound. As it is my mom went through years of depression because she was so reliant on everyone else to get simple things taken care of.
Having a bus stop 2 blocks away helped her get to and from work everyday, and she loved that she was able to lead a normal life.
Now, we didn't live in Lincoln Park. We lived on the south side in a residential neighborhood. If my mom needed to run errands, she had to walk to the bus and the bus would take her a little further into the city. It was a bit of a PITA but Chicago is a city of neighborhoods and each neighborhood has a different feel. My parents chose to be in a neighborhood that felt a little more like a suburb. We had a large yard (for the city), a driveway, and ample parking in front of the house. But further north, toward the Loop/downtown and on the north side (Lincoln Park, for example) there might be fewer homes with yards and parking can be a pain. Some neighborhoods are more family oriented, others are for the young a hip. For example, Lincoln Park has a good balance and one can raise a family there or be young and trendy. Lakeview/Wrigleyville is NOT a family neighborhood. It's a fun neighborhood, but it's not a place I'd want to raise a family unless I wanted a 4 year old who knew which bars had the cheapest cover charge. It's mostly bars with Wrigley Field in the middle of it.
The far north side and the south side have some great neighborhoods for raising families. I live near Midway Airport in what I would call a residential neighborhood, but thanks to the airport there are plenty of business and restaurants within walking, biking, or busing distance.
You can even live in a close suburb (one that boarders the city) and still have access to Chicago buses. The Chicago transit and suburban transit companies work together so you can take a city bus out to the suburbs (but not too far out).
It IS possible to live in the city and raise a family and raise your kids to be strong, capable adults. Daycare can be affordable but it depends on where you look. Many downtown buildings have on-site daycare. A good friend pays $30 a day for in-home daycare. It all depends on where you're willing to live and what you can afford. For example, I'm willing to live on the south side, and because of that my rent is about $400 cheaper a month than someone who lives in Lakeview or Wicker Park. Sure it'd be nice to live in a trendier area, but as you can see from my siggy pic I'm not very trendy or hip. :-)
I hope this helps answer some of your questions. After reading your posts I felt like your stresses and concerns were those of my mom, and I could relate. If you have any more questions, feel free to get in touch with me via my blog (link at the bottom of my siggy) because I'm not on the nest all that often, but a friend told me to check out your post on the Chicago board.
Good luck!