As it is, I find it hard. If you stick to bundler/npm/etc would there be benefit it not only notifications but an automatic update feature? Tie it to git where possible to have a "newest" branch that keeps this out of master and/or tie it with the likes of Travis CI to make sure things didn't break. There's almost too many moving parts but I see high value in keeping a project on the latest dependencies without much involvement from myself. Its not foolproof though and may be too error prone to pull anything off without pulling your hair out.