I resisted the switch from Winamp to iTunes for as long as possible. When I got my iPod Photo, though, I lost the war. iTunes was needed in order to be able to synchronize photos to the device which was an important feature for me, especially the album art. Over time, I’ve gotten used to iTunes and forget what I miss from Winamp. The fact that the original team is gone from Nullsoft made the loss of Winamp seem less severe after all.
While I sync my music library to my iPod using iTunes on my Windows desktop, I also wanted to keep my contacts and calendars synced. To do this, I had to use iSync on my Powerbook. My Palm bridged data between my Desktop and Powerbook, while iSync then brought that data onto the iPod from the Powerbook. It was a bit of a convoluted system, but it worked extremely well as long as I synced my iPod up to my Powerbook about once a week.
When I updated my Powerbook to OSX 10.4 Tiger, it pretty much broke my ability to sync my Sony Clie NX80V with my Powerbook (extremely frustrating). Because of this, I quit syncing my iPod with my Powerbook because there was no way to get the new data over there. Basically, it threw my iPod out of the loop. At least I had my music and photos.
So why am I explaining all of this? Well I’m a bit excited, because tonight I see that there is an update to iTunes, bumping it up to the 5.0 revision. In 5.0, they have added the ability to synchronize your iPod with Outlook on Windows. While it’s not exactly what I want yet, which is Palm Desktop synchronization, it is certainly a step in the right direction. Having my iPod sync my calendar and contacts with my Windows desktop would eliminate that nasty cross sync between my Desktop and Powerbook.
Although, here’s where I flip-flop… I do like having my Powerbook and Desktop synced up as far as calendar goes… and I just got a Palm Treo 650, and I will have to see how it plays with OSX Tiger. Hopefully I’ll be able to hit a Bluetooth hotsync between the Treo and the Powerbook every now and then, and everything will stay synced up. Mainly though, I can put away my iPod’s firewire cable. 
[/rant] I hope at least someone followed that.
Sounds like a good plan by me.
Perhaps my biggest excitement about getting a powerbook is having embedded bluetooth so I can really help make my self more mobile!
Good luck man. Let me know how the T650/Tiger combo works.
And now, PalmSource has been bought by Access, a Japanese phone company.
:: sigh ::
Sadly, I gave up on Palm a while ago when I heard one of their key execs say ‘wireless isn’t interesting for our customers. we have a wireless model and it doesn’t sell well’.
She was talking about that ugly klunky palm with the ungainly fiddly keyboard. I hope she’s fired now.
Anyhow, I’ve been an iTunes convert for a while now, and here’s a golden tip: Find and backup your iTunes database on a regular basis.
If something goes wrong, all your carefully collected ratings and play data go down the drain. If you switch computers moving the itunes db is doable, since the important bits are all XML. A simple search and replace for drive paths and you’re good to go.