Dave Caolo have posted some explanations on how he uses text files and tags between iOS and Mac OS X, and how he adopted the ‘everything bucket’. It is worth reading. About tags, here is one thing he wrote: (…) dump everything into a single folder and use tags to keep things sorted. I had two problems with that solution. The first is that Notational Velocity and Plaintext don’t support tagging. The second, more powerful issue was my stubborn adherence to nested folders.

I may be wrong, but I think one can use tags in Notational Velocity, and that it works fine with Simplenote. But that’s not the point I want to discuss, which is tags and tagging in general, and how to play it safe.