I use SquareTrade, not because I want to Jailbreak my device, but because they have the better warranty. If you fully immerse you iPhone in water (drop in the toilet) it is not covered by AppleCare. SquareTrade will. Their warranties cost about the same as Apples and cover more.
I am not a fan of jailbreaking your iOS device mainly because it is a hassle and you are opening your phone up to more instability and possible hacks (if not done right). I also have not found that many apps that I just have to have without jailbreaking. Apple usually has a pretty good reason for not alloowing them.