I'm on my 3rd iPod now, the 60Gb photo version. My second one stopped talking to my PC a long time ago and I was stuck listening to the same playlist for so long I stopped using it altogether. I can't believe how glad I am to have mobile tunes again!
Plus, I found a little app for Windows that synchronises the calendar on the iPod with my Google calendar, which coincidentally I've recently started using in anger. It could be more plug-and-play-like, but it works.
So I'm looking forward to a weekend of CD ripping!