Based on Rob's comments and the comments in the Lifehacker thread he pointed out, I'm going to try out SVanKruistum's iTunes Tagger (beta).
- Does most of what I want out of the box, and is free.
- Auto-tags selected songs in iTunes with top tags from last.fm, thereby taking advantage of that existing folksonomy (and its problems, too - see Disadvantages).
- Allows me to create my own smart playlists based on the tags it populates into the comment field.
- I don't use the Genre field very much, but this'll update that too
- It's possible I will discover new/better ways of classifying or tagging tracks
- Similar Songs playlist maker with slider bars! Initial tests look promising!
No tag-based navigation, such as a tag cloud, to help me discover subpopulations of my music.- nevermind, there is a tag cloud feature but it isn't fast across a large library (but that's no surprise, how could it be?)
- Using the comments field means I can't select a bunch of songs in a playlist and just add a tag to them all without screwing up existing tags.
- Grabbing the most-popular tags from last.fm means I'll end up with almost all songs containing at least one of the following tags: rock, alternative, indie, or pop. These are not useful tags from my perspective.
- Automated tagging brings the disadvantages of folksonomy too, meaning I will get weird, non-useful tags on some songs (but that's still potentially better than having to do every song myself).
- I would have preferred open-source, in case I felt the need to tinker.
- Flow of tags is unidirectional; any custom tagging in the comments field I do won't automatically make the app better for everyone by uploading those tags to last.fm - I'd have to do that in a separate step, which means I almost never will. Update: this may not be true - He claims to have added a way of making doing what tweet does and allowing the tags to flow back to last.fm via a tagger in the system tray, but I haven't figured out yet how to access this feature.
- I've already come across several states that will crash the app, but these are feasibly avoidable once known, like the dangers of the Fireswamp.
I may also try out Tweet, a tagger that will sit in the system tray and allow me to easily edit tags as I listen (not clear at this point if Tweet is comma or space separated, which may or may not matter for interconnectivity with SVanKruistum's stuff, which uses comma separation).
Now what I need is an army of outsourced workers in India or somewhere who understand my musical classification scheme (no small feat), and who can tag the untagged songs and prepare the library for me to sweep in and make excellent Smart Playlists! After they're done with all the other data-entry and classification work I have in mind for them.