To sync or not to sync...

This is making me feel very old, but after using an iPhone for over a year and mac products for many more, I still feel shaky on the subtleties of syncing. Am I asking to much to be able to sync to more than one computer without losing everything? I have a work Macbook Pro, A desktop PC, an iMac and a windows netbook, I use all of these with practically equal regularity. I find myself needing to add a file from one machine, take off a file another, sometimes I am on the road and may take one of 3 computers. I also record music on both my desktop PC and iMac and use tracks while playing shows/touring. The last tour I was stuck because I couldn't add backing beats to my iPhone to use for the next show because my phone was synced to my desktop PC. It is really frustrating for a person who does not have a "home base" computer, but rather a a series of computers to fill specific functions, of equal importance and necessitate usage with my iPhone. I am prepared for(though not happy about) the probable response of, you purchased a Mac product, deal with the restrictivness of iTunes." It just doesn't seem to be beneficial to limit it like this. Any suggestions as to how I can work around this?
Cheers,
Eli

Each time that I have checked that off to manually manage music and videos it  warns that everything will erase and sync to the new library when I attempt to apply the change.

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