I've lurked here for years, and this finally brought me out, so Hello World!
I've lived in Richmond for the past 15 years. We live near Stony Point, which is just south of the James River, but still in the city. It depends on your family situation where you want to live. If you're single, there is probably more to do in areas like the Fan, or Downtown. If you have a family and school aged kids, look for something in Chesterfield county - schools are good, but more traditional suburban developments and malls. We have a 2 year old that we'll need to make some decisions about where he'll go to school, because the city schools are not that great. Chester is probably a good bit more "southern" than Richmond, but I don't get down that way very much. I would think if you picked somewhere west of Richmond (Short Pump) - you'll have a pretty decent commute again to Chester - probably at least 30 minutes again.
Hope that helps, let me know if you have questions about a specific area