The winter weather is actually quite fantastic in the winter. Calgary likely gets the most sunshine in all of Canada, and the winter time will have long periods of above seasonal temperatures with day time temperatures above freezing (these are called Chinooks). The city sprawls quite a bit, so travel time across the city can become difficult.

There's lots to do in and around the city if you're active. There's a great river valley pathway system that you can use year round for cycling, jogging, or exploring. Canoeing in the summer, ice skating in the winter, skiing and snow shoeing in and around Calgary. Plus it's only an hour to get into the foothills, the rockies, or the prairies. Lots of places to go explore outdoors if you're active in any way.

CUFF is great, CIFF is alright (I much prefer CUFF). Overall, a decent amount of culture in Calgary, but it can get expensive if you're not careful. Lots of big bands skip Calgary in favour of Edmonton or Vancouver. Calgary's a safe city. Even the seediest neighbourhoods in Calgary are safer than a lot of cities. There aren't any issues with being an out gay man in the city. Gay culture is pretty lackluster in Calgary. Those who don't like to go out to the few clubs (with some overly dramatic, bad history) tend to quietly segregate into their own friends network.

Tons of good food in Calgary, but like every city, you can pay a lot of money for mediocrity. Galaxie Diner, OEB, Palomino, Pigeon Hole, 10ft Henry, Rouge, are all fantastic places to try out, to name a few.