Best/worst parts of living in Naperville?
I've lived in Naperville my whole life.
Schools are great.
Downtown is a great place to walk around, especially the riverwalk. It's always crowded in the summer with people packing into restaurants. A lot of teenagers frequent downtown. A lot of places seem to be closing or have closed in the recent past.
Like someone else commented, avoid the condos on E Bailey. I believe they're called "The Olive Tree Condominiums " or something similar. Also avoid any housing in far north Naperville by 59. There has been some shady stuff there too.
No matter where you live, you will be in close proximity to a Jewel, as there's four of them: W Ogden and Aurora, E Ogden and Washington, 95th and 59, and Naper and 75th. Casey's Foods (Gartner and Washington) is a popular place too with excellent meats and other selections. Trader Joes in the same strip is also popular. It's probably a drive for most to go to Walmart on 75th, it's way out of the way. Then of course you have other stores and plenty of restaurants to choose from, especially along Ogden and in Downtown.
As for parks and forest preserves, there is: McDowell Grove (north part of town), Springbrook Prairie (south of 75th between 59 and Modaff), Knoch Knolls Park (closer to Bolingbrook), and then Frontier Park (south part of town), Knoch Park (central part of town), and Nike Park (north part of town). All of these you should check out.
I can't say much about housing, except that lots of older houses (usually split levels) are getting torn down and huge monstrosities are taking their place.
The big culprits for traffic are 75th between 59 and Book Road, any part of 59, parts of Naper south of 75th as well as closer to Ogden, and lots of areas along Ogden. At least along the E portion of Ogden, trying to turn left out of a business might be an issue.
Overall, I'd rate Naperville 7.5 out of 10.