It really depends on what you would like your phone to do...a stock phone is completely fine to many people, but to others, they want a little more from their iPhone's. It may also depending how tech savvy you are....for instance, most of the good themes to change the way your phone looks requires a lot on your part to be able to use something like iFile to mod the theme....it can also get frustrating when it comes time to restoring from a jailbreak...changing hosts files and such, can get pretty messy if your not handy with your computer. I've been jailbroken for most of the time, but I'm actually ok on ios5 without the jailbreak....I'll wait till I get bored with it before jailbreaking it again.