You forgot Melrose and Winchester! I live in Melrose - love it. My cousins grew up in Lynnfield, the loved it. I have a friend that teaches school in Reading - it has better schools than Wakefield or Woburn - Woburn is a bargain (cheap). If I had to pick of the 4 and you can afford Lynnfield go there. If you want to save some money, go to Reading.
I have lived in 3 of the five towns. I have a 2 year old and just moved to Winchester, our first choice of towns, but reading was a close 2nd. If the right property came up in Reading we would have bought there.
Strictly my opinion. We wanted to find good public schools with what felt like a real community.