You could definitely be in worse places, Cheltenham's a pretty good place to live.
There are no more Chav's than your usual mid sized town, and the crime rate is relatively low. There are some nice eateries around, and some fairly good pubs too.
As for punting, it does vary - I'm sure it was better 10 years ago, but I had a lot more disposable income 10 years ago so I was seeing more expensive escorts, and I was actually out of the game for a few years until recently. There is your usual crop of Romanians who I have found to be lacklustre at best, and there is a group of Polish who seem to rotate around various towns that are better (
External Link/Members Only) - I have a bit of time this week so I plan to review the ones I've seen.
There are still more expensive girls around but none that I've seen. One that I intend to when I have the £'s is
External Link/Members Only in Gloucester who is a former pornstar and well reviewed on here.
Other than that as mentioned above Bristol seemingly has a better selection and I had a couple of decent punts in Birmingham, but again that was a few years back before my recent 're-entry' into punting after a few years hiatus.
On re-reading that's possibly not too helpful, but I tried!