If it is the mountains you are interested in (snowboarding and winter resort and area activity) Then the Denver area is going to get you much closer to them. There are mountains in the springs, but not the ski areas. Your watersport activities are also much more likely in the Denver area. Pueblo res is not a bad spot, just can get a little hectic on the weekends and a 45 min drive can also get you down. But not everyone can live 8 blocks from their lake like Me
I am not a big fan of Co Springs myself. No bashing needed, just too religious of a town and a HUGE pain in the butt to get around town. The people are friendly, and the scenery is very nice. There are just too many religious zelots that inhabit the area.