What size? Is the iPod Photo worth the extra bucks? How many songs from your library do you sync?
Given the size of your library you have two options: either you want to synchronize it all, in which case you should go for the 60gb iPod photo, or you decide to synchronize only your favorites, in which case the mini (one of the new 6gb ones maybe?) would be a better option.
I personally have a 40gb photo iPod and an MC library about the size of yours. Although I wish I had a 60gb to fit it all, I followed Larry Little's guide (
http://www.jrmediacenter.com/Larry_Little_iPod_Management_MC.html) and managing the sub-list of songs that should go on the iPod is now a breeze (especially compared to iTunes with which you'd have to uncheck one by one all the songs you don't want on the iPod). But the easiest way in my case would certainly be to have a 60gb iPod and synchronize the whole library.
Any problems syncing w/ Media Center? I still want to use it, I like it more than iTunes...
MC is definitely better in many respects and there's no going back to iTunes once you've tried it. However, there still are a few things that iTunes does and MC can't (for now):
_ MC can't transfer photo and music cover art to the iPod (that's a big one)
_ MC can't auto-mount the iPod (if your iPod is plugged in but not mounted you have to unplug it and plug it back for MC to see it) and can't auto-eject after sync (although it can auto-eject when MC closes)
_ MC doesn't recognize different iPods as different devices
_ file upload to the iPod is a bit slower with MC than with iTunes (at least that's what it seems like to me)
I can't list everything MC does better than iTunes, that would be too long. Just a few things:
_ it can convert from many formats when syncing to the iPod (iTunes is limited to MP3, aac and apple lossless)
_ MC can play songs from the iPod (iTunes can't)
_ MC can transfer back songs from the iPod to a PC (iTunes can't)
_ much better smartlist system
I also use an iMac at work, can I sync w/ both? Do I have to sync at work, or can iTunes read directly from the iPod w/o copying files? Is that even a good idea?
Your iPod needs to be "initialized" by MC to work with it but afterwards iTunes will still see your player and be able to communicate with it. As I mentioned above, iTunes can't play songs from the iPod. In addition, and this is more important in your case, I might be wrong but I think that once an iPod is formated in FAT to work with a PC you can't read from it using iTunes on a Mac. Even if you can, iTunes won't let you copy songs from the iPod to the iMac and won't even let you play songs from the iPod. My advice would be to look for another program for mac that would let you do this since you can already forget about iTunes.