You sound like a pack rat to me! Haha just kidding
you just seem like you like to have a lot of stuff with you, I guess.
I'm around my computer enuff to where I can just sync what I need. I actually like syncing often as it keeps my address book up to date across all my devices (yea yea, I know, buy mobile me)
I have tons of content as it sounds like you do as well, my main point being that I just don't need all of it with me all the time.
When I sync my iPad I put on what I'm gonna need "today"
My uncompressed music of only about 800 songs (down from 1000) is over 25GB alone.
I also have a lot of Cisco PDF's which range in size from about 30MB to a couple hundred MB. I have a bunch of Cisco Press books through the Kindle App, as well as tons of word and excel files for work. My apps are just over 1GB right now. I have never counted, but I think that I have around 100 and use just about all of them at least once a week, except the 15 or so games which actually get used a lot less because I am too busy with work or the forums.
I also have my iCal synced along with my Google Calendar. My contacts are only from my Mac since I do not keep any contacts in my Google Contacts.