So I’m no longer living on the edge. I’ve traded in my jailbroken features for iOS5. For me it’s worth the upgrade. I miss the Android Lock and hiding apps, otherwise I’m 100% happy with the upgrade. iMessages is cool, Reminders will be handy for it’s location aware stuff and the new notifications are awesome (better then the hacked jailbroken version, obviously!).
My big annoyance right now is that an old bug seams to be back. Used to be that when you’d sync a Smart Playlist the order wouldn’t copy properly. I can’t remember how long ago this was or when it was fixed, it’s was super annoying and it was fixed a while ago. I’ve only got one playlist where I care about this is my Podcasts. I like to manage the order in which I’ll hear them. Moving daily stuff up so I’m never as far behind. That bug seams to be back, the only solution is to turn off “Live Updating” which negate the advantage of a smart playlist!
I hope with is fixed quick and that it only takes an iTunes update. I also hope the jailbreakers break in soon too!