I'd say look at the north-west, and my favourite city would be Lancaster (well I lived there for 7 years so I would). It's small enough to be friendly, but has a huge student population so there's plenty going on. There's also all manner of theatre, art, art-house cinema, sports, and strange weird groups meeting in tiny pubs. Property still isn't that expensive, you're ten minutes from Morecambe bay, one of the finest there is as far as I'm concerned with the veiws across to the Cumbrian fells which are 40 mins or so up the A6, then there's the Fylde coastline down to Blacpool, very flat, but fantastic roads in their own way, and the Forest of Bowland is just out the back, with yet more great roads. There's also (or there was) a big biking scene with plenty of people riding out on Sunday mornings to various watery places.
Mancester's not far away either if you want a big city, Scotland's a couple of hours away tops and Yorkshire is just across the border, but we don't talk about them.
The only downside, it can be a bit rainy, but when it's not it's often sunny (Morecambe Bay has it's own microclimate).
Oh and you can get a ferry from Heysham to the Isle of Man for the TT
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