What I need is to be able to search for something else (which I
believe I could do by searching using a regex), but I would like that
second thing to be in another color a la Google's search results (at
least in dejanews). What I need, eventually, is an angry fruit salad
of colors for all the search items I've entered.

Is this currently doable, and if not, do you think it's possible to
accomplish using a plugin?

I think this plugin will accomplish what you want:
http://www.vim.org/scripts/script.php?script_id=1238

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