All depends on what work you're doing to be honest. I moved to Calgary from the UK in the summer and it's been great. Sure I wish I was closer to the mountains but then I'd be commuting over an hour to get into work through the week. Still - coming from a guy that used to drive 6 hours to ride fucking Scotland I'm in heaven here. 1 1/2 hrs to sunshine - 1hr 45min to LL - 3 hours to Kicking horse.
My honest opinion would be to get the RCR pass which gets you into Lake Louise, Kicking Horse, Fernie and Nakiska. I'm not sure if they do half season passes - which might start in February. Sunshine is fun - but it's a gong show every weekend - with a lot of flat and tracked out terrain. I think from Feb the snow at LL will be worth the extra 20 minute drive.
Also - I've only been to kicking horse once but I'm going back next week. It's a nice 3 hour, scenic drive and you can stay there for pretty cheap if you make it a weekend trip. The Dreamcatcher hostel is more like a B&B and it was $33 a night. If you want to splooge more there are shit loads of owner rented chalets and condo's - plus hotel style accommodation on the hill.
It's the best place I've ever rode to be honest, including a season at whistler blackcomb.
As for Calgary itself - the place has a surprising edge to it. I was expecting more of a straight laced, conservative oil town but there is a thriving sub culture here. Lot's of live music and good nights out. You get some good gigs at Republik and The Broken City.. Mid week wings nights - my favourite is 'wingo' at broken city. If you skate there's a big outdoor park downtown by the bow trail which is good through the summer. Also you're very close to excellent mountain bike terrain - in the city limits there's nose hill and fish creek park which are both pretty tame but still fun. If you drive out 45 minutes you're in kananaskis country which is come of the best mtn bike terrain in the world in my opinion.
It does have that straight laced aspect though, people here can't drive for shit, I encounter too many racists at work and I personally thought the stampede was ridiculous - but that's not all Calgary has.
Still the big draw is the snow and the hills - but there's still plenty to do on those down days.
If you want someone to ride with when you get here PM me as I'm new(ish) too and most of my friends here are either complete beginners or skiers. I recently had my brother and friend over from London for 3 weeks - I forgot how good it is to let loose and shred properly.
Hope this helps.