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I've had an iPhone now since March 2007. I previously used a Nokia E90, and before that I had a Nokia 9300, which replaced my Psion Series 5, and so on into the mists of antiquity. I really am a power user when it comes to PDAs :-)
It took me about two years before I could pension off the Nokia E90 (except I still use it for sat nav when I'm not driving my own car, and as a modem to my Apple MacBook occasionally). That was because Apple took so long to implement obvious features like Cut/Copy/Paste and for me to be able to record my expenses in a timesheet and my work notes in a word processor - thank you DocsToGo!
So what still drives me nuts on the iPhone? Top of the list is the insane complexity of syncing calendars with iCal on my Mac and Google Calendar. I haven't dared to try syncing to Google Calendar since it has been so hard to just sync the iPhone to iCal. Basically, it just doesn't work properly. My Iphone has one Mac calendar, which works ok, and one calendar for each of my imap email accounts. I managed to sync To Dos and Notes through the imap calendars, but if I add an event to an imap calendar on my iPhone, then sync to iCal, it doesn't appear in iCal, then the next time I sync, it vanishes from the iPhone.
Frankly, this is total rubbish! Why can't Apple sort this out?