Jeff Atwood laments the single-item nature of the Windows clipboard, and points out utilities that can expand the capabilities to multiple items. I think that’s a great power tool to have, but I’m not sure having a multiple-item clipboard is really the best thing.
I think one of the strengths of the clipboard is its single-mindedness. You always know that the thing you’ve copied is what you’ll paste (even if it is stored in multiple formats in the clipboard, it’s al conceptually the same). Once you expand the clipboard to contain multiple items, will the average user be able to handle a menu popping up asking which item to paste? No, probably not. That’s why the utility he mentions only pops up that menu when you hit it’s special shortcut. That’s the way it should be. It’s a great thing for advanced users, but I think of little benefit to the average.
For me, the simplicity of the clipboard is a good feature. Even if I had the extended capabilities of a clipboard that held multiple items, I probably would still use the basic functionality most often.