Thanks to all who replied with suggestions. A lot of my issues stem from simply not being familiar with the software. Since I post, I’ve become a lot more adept at using it effectively.
As suggested, working in “chunks” seems to be the best way to use the software. That eliminates the issue with long wait times while the software downloads information. Specifically, I’m mostly working with single albums or artists at a a time.
I doubt my situation is unique so I’ll add a few tips of my own. To set the stage, my digital music collection has become scattered over the last couple of decades. I put my trust in a few other pieces of software aimed at eliminating duplicates, fixing my tags, and just helping with overall organization of my files. Some of these software packages did a lot of damage to my collection, shuffling tracks to the wrong album, isolating single artist compilations into folders away from the main artist folder (Thanks iTunes!), or even nuking tracks with similar titles. I made a few backups here and there, but none of them are complete.
So I’ve been using Picard with a couple of other pieces of software: Everything (a file searching utility), DupeGuru (if it’s not obvious from the name it finds duplicate files), and RED (Remove Empty Directories)
At this point, I have a bunch of folders from old hard drives, each of which contains a copy of my collection form some point in time. If I was able to start over, I’d use DupeGuru to scan all of the folders for exact duplicates, with my “current” collection set as a reference. Then I’d have DupeGuru remove all non-reference duplicates.
Next, I’d use RED to remove all the empty folders left behind form the process, just to make it a little easier to navigate and see what’s left over.
At that point I’d fire up Picard, and start working one artist or album at a time. I’d drag the artist or album from my current/reference into the program and let it do it’s thing. After handling any unclustered files, I’d start working my way through the missing tracks.
This is where Everything comes in. Windows file search is awful. It often fails to find files that exist and is useless for searching multiple large folders. Everything can take up to a minute or so to build it’s database (it catalogs the entire file system) but once it’s built, search are blazing fast. I go through the missing tracks one by one, typing all or part of the song title in Everything’s search bar. If it exists in any of the “backup” folders, it will show up. If I find a missing track I can drag it directly into picard from the Everything interface.
Finally, I save the completed album to a new folder (I just called it “MusicFinal”. The destination is set in Picard Options under File Naming, Destination Directory.)
Anyway, thanks again for all the help. If anyone has any questions about the other tools I’m using, feel free to ask.