I would probably use a hybrid of the two. Use the tag system for things I've tagged, and fall back to a regular filesystem for untagged files. That's basically

I would probably use a hybrid of the two. Use the tag system for things I've tagged, and fall back to a regular filesystem for untagged files. That's basically how I have Steam setup. Most of my games are tagged, usually with multiple tags, and all untagged games just go under Games. Once I got everything organized (via automation, not manually -- not necessarily relevant, though), keeping up on tagging new games became easy and quick. I imagine there would be automation tools written for a tagging filesystem, that just "knows" a lot of common software, etc., and can get you started.