Will my blackberry calendar sync with my outlook calendar automatically or does it have to be plugged into the computer to do this?
Must be plugged in and synced with Desktop Manager. You can try google sync to sync your outlook with google calendar, which can also sync with your bb. however, google calendars and outlook don't communicate well when it comes to recurring appointments.
I had an iphone for 3 months but came back to the blackberyy. that was the only thing i liked about the iphone. If i put something in my iphone calendar it was immediately on my outlook calendar at work.
As stated above, download Google sync for your BB and also for your PC at home. It will wirelessly sync your BB to your Outlook via Gmail. It works great on my device.