Pros
City Year across the board does amazing work. I wish that it had 10 times the funding, as it is meeting a critical need, by providing positive mentors and role models to students at risk of not graduating high school in 4 years, or at all. As far as non-profits go, it's extremely organized, and constantly working to improve its methods.
I'm nearing the end of my second year with City Year, and am extremely grateful for the experience and growth it has given me. I've grown so much in my time here. Your City Year experience is what you make of it. If you understand and work with the culture pieces, and take advantage of the resources within the organization, City Year can be a life changing experience. If you fight the culture pieces (especially the uniform), you're going to have a very difficult year. Expect to work hard, and don't plan on being out of work before 6:30.
City Year allows you to work on diverse teams of 8-13 young people in under resourced schools, tutoring and mentoring students. These kids are some of the most inspiring people I've ever met. Your team makes you stronger.
Within City Year, there are AMAZING, talented people who work very hard to further City Year's mission. I have learned something from every single person on our staff.
Cons
Sometimes City Year does make things more difficult or stressful than it needs to be. During initiative heavy times of the year especially, the corps is exhausted.
The stipend is rough to live on, but there are ways to make it work.