All of the towns mentioned are quite nice places to live actually, crime is low, easy access to the countryside, well served town centres. From Guildford the train to Waterloo takes about 35 mins and goes every 15 mins approx. Guildford has quite a lot going on for it's size, Guilfest music festival, Surrey County show, cricket matches, lots of sports clubs.
From Guildford I can ride to Tunnel Hill, Surrey Hills, North Downs and the Devils Punchbole areas, so don't need a car to get a good ride out. The university is pretty big in Guildford and has recently opened a big new sports centre that's open to the public. The town centre has some good restaurants and pubs (the George Abbot is good for watching the rugby, I think it shows live tri nations matches). A couple of area's in Guildford that aren't too desirable to live in, Park Barn and Bellfields, but they're really not that bad. Lots of very nice areas. For around a grand a month you could buy a house/flat.
You also have lots of very attractive villages around Surrey but I wouldn't like to say what rental availability is like. These smaller villages seem to all have huge houses that command huge rents.
And the riding is far far better from Guildford :D