This vim plugin seems to do most of what you describe by wrapping the matchadd() vimscript function:
http://www.vim.org/scripts/script.php?script_id=2666
<Leader>r (regex) to add matches to the set of highlighted groups.
http://www.vim.org/scripts/script.php?script_id=2666
<Leader>r (regex) to add matches to the set of highlighted groups.
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