So why did I hold out so long before upgrading to iOS 5? That’s because the jailbreak was just released today. The main reason for holding out for the jailbreak was that the inability (even in iOS 5, sadly!) to silence notifications at certain hours of the day (night). Silencing the notifications required installing the jailbreak app SBSchedule.
For me, the trickiest part was figuring out how to manage the whole iCloud functionality, when until now my wife and I had been sharing a single Apple ID. I didn’t want to have my phonebook mix with hers, or vice versa! But this article had a great discussion about the topic. The readers digest version: continue sharing the existing Apple ID for music and apps, but create new individual iCloud accounts for all the other features.
I won’t be using iCloud to synchronize my mail, contacts, and calendars, since I’m using Google Sync to do that. But finally, Google sync now supports sending from a different email address! This works great for those of us who are using Gmail interface but who would still like to continue to our own domain name for our email address.