I'm not jailbroken and probably never will be. I just don't see what positives it would offer me whilst meaning I couldn't update as and when updates come out.
It does what I want it to do and so far I haven't thought or heard of anything that jailbreaking would allow me to do that I really need or want.
As always, what ever works for you is best. I felt the same way for a LONG time.
For a long time I was intrigued by JB'ing, especially some of the cool themes but was concerned about all the usual issues. However, after spending a few days reading up on it in my spare time, I took the plunge. Now I can't bear the thought of going back.
I use my iP4 all the time. It's in my hand nearly 6 hours a day and in front of me on the desk or bedside table the rest of the time. On a typical day, the following JB tweaks get used dozens of times:
SBSettings: Swipe across the top of the screen for drop down toggles that provide one touch access to BT, WiFi, Brightness, etc. I'm constantly turning these on and off and adjusting brightness throughout the day. Coupled with SBSchedule which provides quick access to Profiles of various settings (volume, BT, wifi, brightness) for different situations with a single action. Fantastic!
LockInfo: A hundred times a day I just glance down at the lock screen to check email, calendar, and twitter without having to unlock the phone. Priceless.
VoiceActivator: Let's me define dozens of voice activated shortcuts for use when the phone is out of reach like when I run or am on the bike.
3G Unrestrictor: FaceTime with my kids over 3G while traveling is magic.
As to being able to update the second Apple drops a new firmware version, that's HIGHLY overrated. Waiting a couple of weeks for the JB team to respond is a small price to pay.