We are from WI and have lived in both Gilbert and Chandler. We lived in Gilbert near Ray Rd and Cooper Rd. for 6 years and now live in Chandler near Ocotillo Rd and Cooper Rd. We moved about 5 miles south and have lived here for 5 years. We are in Cooper Corners West. I would say that there is not much of a real difference between the two cities. The property taxes are lower in Chandler because there is more industry to offset the costs of the city. Actually we have lived within 1 mile of the border between Gilbert and Chandler in both homes. Chandler does year round schools while Gilbert is still on the older system of having 3 months off for the summer. Our daugher is only 2, so I don't really know too many details about the schools. I have heard that our neighborhood is more desired than most since our kids go to the San Tan Elementry School which ranks quite high. Also we are about 2-3 miles from Hamilton High School.
The homes in our area are medium to large and can easily accomodate a family of 5. I would say we don't have many "starter" homes. Some have basements which are not very common in AZ. I would say that you really want to try to be close to work if you can arrange it. Traffic can be quite bad depending on where you are going.
We are also only about 3 miles from Tumbleweed park and about 8 miles from San Tan Mall and Chandler Mall.
I can give you so much more information if you want to contact me directly. I also have a good friend who is a real estate agent if you have not already found one to work with. Just let me know.