on the town centre bit, Woking's town centre is quite compact and has little character in that all the shops are chain stores. OTOH, there are quite a lot of shops, and lots of people spend their time taking kids in pushchairs from Starbucks to Debenhams via H&M and Next or whatever.
The dining situation is pretty poor, there are some fast food places, a few Indian restaurants, some low-end Italian restaurants, and a few Chinese takeaways.
Guildford has better on this front (more places to go, tend to be slightly more sophisticated), much more in the way of independent shops, boutiques.
I guess WOking and Redhill probably have a bit in common in that they are the less poncey parts of Surrey.
Also in Guildford the chavvy pubs (Wetherspoons etc.) are concentrated by the train station, whereas in Woking the nighttime entertainment is basically Wetherspooons + Yates, which is I think what leads people to suggest that it's miserable.
It's not at all, pretty much anywhere in Greater London would have worse behaviour, but the fact that Yates et al are so central makes them rather dominate the town of an evening.
Guildford is considered considerably more desirable, hence higher rents, but in Guildford there is more traffic to fight through if you want to go somewhere, and the town centre is on a steep hill, which is perhaps not the best with baby in pushchair.