Colorado Springs is a large enough center that it encounters different availability cycles depending on what neighborhood you're shopping in. Typically though, summer is better than winter, and will have more apartments listed for rent. By the same token though, you might have more people applying for the same apartment in the summer, so putting together a good application becomes even more important.
Getting a landlord to accept your application in Colorado Springs is reliant on what you can prove. Landlords can't take your word for things like your ability to pay the rent. Instead, you need to be able to show it. A letter of employment is a very good way to show that you can meet any rental obligations.
The Mountain Metropolitan Transit service provides public transportation service within the Colorado Springs area. However, many people in the area choose to drive instead. There is so much outdoor recreation in the areas outside the city that people like to have a car to access remote areas that aren't serviced by the public transportation system.
Climbing and hiking in the surrounding area is popular with newcomers and locals. Museums and exhibits like the Western Museum of Mining and Industry and the Ghost Town Museum celebrate the history of the area. The area also provides access to some of the best white water rafting in the country. Microbreweries abound in Colorado Springs, with Bristol Brewing Company, Phantom Canyon Brewing and Trinity Brewing all having a wide selection of locally brewed beers.