The first problem I had when I plugged things in and pressed sync is that iTunes decided not to actually copy my calendar, contacts, etc. off. After a few minutes I remembered that you have to actually frob some button in a dialog for each of these. Once I had that figured out I tried to sync it again and after asking me if I realized that I was massively changing the data on my computer (which, remember, knows nothing at this point) it just popped up the useless progress bar and spun. And spun. For hours. I tried this a few times with the same results. At this point I figured I had been bitten by the dreaded slow iPhone sync, and was all ready to start trolling my disk for crash files to delete, slaughter a rubber chicken, etc. when somehow I noticed that hiding under all my other windows was a dialog saying "hey, you know you're replacing the contacts list on your computer with the one on your iPhone, right". Clicking that dialog made everything proceed in a few seconds. Remind me again why that dialog isn't modal? The spinning progress bar isn't exactly the UI indicator you would ordinarily use to indicate that I needed to click on some button. For that matter, why do I need to click this dialog at all? I just installed the operating system: why wouldn't I want to copy stuff off my phone onto my totally empty calendar and contact list?
Curse you, iTunes sync
I recently had to send my Macbook Air in for repair and as a precaution
I burned most of my data off the hard drive. Of course, when it came
back I wanted to restore some but not all of my data. I have Time
Machine backups, but since I actually only want some of the data
and I want new versions of the software, I decided to treat this
as a new machine install. Naturally, I figured I could just use iTunes
to sync my data off my iPhone. In principle this should work fine.
In practice, not so much.

clones dude. you need clones.