I'm merging all discussions about Colorado Springs into this thread here, so people can ask questions or post info about it all in one place 
I winter in Colorado Springs (60 miles south of Denver). It's a great city to be poor in.
Plenty of places to camp. Tooons of christians here which equates to lots of food banks and help-the-hungry programs. (They give away pizza in Acacia Park every Sat.!)
Downtown is small, public transpo is mediocre, and in 15 minutes you can be very far away from people in some of the most beautiful nature I've seen. I cook as well, and have always gotten work when I wanted it. (I do have an AA in culinary though...). Losts of cool communty gardens popping up and a small group of business owners dedicated to doing the right thing by its customers.
-Downfalls-lots of christians, lots of douchy military types (fort carson is close, but this has been good as I have dumpster some amazing gear from apartment complexes). Also no real culture to speak of...a few art galleries, one decent music venue with a good band rolling through every now and again, and only a handful of restaraunts that I would eat at. For me, being so close to the mountains and all the outdoorsy stuff here makes up for the lack of more urban entertaining.
Denver is the only BIG city here. I dont like to be poor in big cities. Just not my thing. You also might wanna check out Fort Collings, a smaller college town (CSU) that has a cool Colorado vibe to it.
I'd look into the Springs or FoCo before Denver....
The website was on the news today. It talked about how people are using this website to relocate to Colorado. Being from Colorado ever since legalization of weed locals have not been too kind out tourist. In fact they are gentrifying alot of Colorado Springs just like Denver to get rid of the homeless. I think the homeless get a bad rep because of the major meth problem and the increase in sexual assault. It's also sad going to some places and seeing how trashed the homeless have kept some places. Please take care of our beautiful state.