I'm finishing up a masters here in the Springs at UCCS so I've got some good experiences.
Transportation:
Beucase I didn't have much money, I went without a car for most of the time I've been here. It was extremely difficult to do because the bus routes are poorly laid out and slow. You usually have to transfer buses to get anywhere and it can take over an hour to get somewhere that would take 20 mins. by car. They buses also don't run late-- they stop running around 6-7 pm. So I strongly recommend having a car.
Restaurants and Bars:
The town itself is alright. It's very spread out but there are some fun bars downtown for both older and younger students. There's also a lot of cheap dive bars throughout town. Being from AZ though I think the Mexican food is terrible. I was also surprised to find out about the dearth of pizza places and late night restaurants considering the high number of universities in the area. There are a lot of places that roast coffee locally and Colorado is known for it's high number of local breweries so if you like craft beer, there is an abundance. Poor Richard's downtown has great coffee and wine/beer as well as live jazz on the weekends. Brewer's Republic is a favorite of mine downtown. It's a little bar which serves only craft beer from CO and the staff/owners/patrons are really friendly.
Political Ideology:
I'm a pretty liberal guy; I'm an atheist and a socialst who is tolerant of other people's beliefs. That being said, Colorado Springs' very conservative nature doesn't have to be bothersome. I've meet a number of similarly minded people through the university (I'm in sociology, a particularly liberal-mided field). There are a lot of military folks and religious conservatives here. Some of my best friends are in the military and are actually quite liberal. There are a couple of bars and social scenes that I have learned to stay away from because they tend to attract a conservative or religious crowd. If CSprings ends up being too much for you though, Manitou Springs is about 20 minutes away and is known as a "hippie" town. It's easy to drive from there to attend school in the Springs