I've lived in Dorchester for the past four years. Personally, I love it. It's about 19,000 people, with some nice old houses, a pleasant high street and shopping area, and plenty of little quirky places, including regular markets with local produce, the world's best coffee shop, and a Michelin-starred restaurant. It's got a lot of history, a lot of museums, a lot of Thomas Hardy (it's his Casterbridge), a good sense of community, good restaurants both chain and independent, it's walkable, the people are not especially friendly but they're not rude either. Interaction with strangers is civil at worst and pleasant at best. The main downside is that it is expensive to live here. Most of the population is pretty affluent and a lot are retired. We've got two Waitroses but no Morrison's and only a mini-Sainsbury's. There's a new Lidl, though, and a Tesco. Decent houses start at about 250k and flats are not a whole lot cheaper. If you're looking to live in a retirement community, though, you'll have your pick. There's also a new development that's pretty nice and has lots of new-build flats and condos available. We also have
Poundbury, Prince Charles's idea of a traditional village.
In terms of transport, it's a quick jaunt to the motorway, about 2.5 hours to Heathrow, and Southampton airport quite literally could not be more convenient. You get on the train at Dorch, relax for about an hour and twenty minutes, get off the train at Southampton Parkway, cross the platform, walk two minutes, and you're in the airport.
I work in Bournemouth, which means a long commute that I hate, and DH and I keep saying that if he can find a job in Bournemouth (he works in Yeovil) we'll move down there. Yet, as practical and in many ways desirable as that would be, it breaks my heart to think of leaving Dorchester.