Thanks for weighing in! It sounds like some of the tagging features are reason enough to upgrade, so I will probably take advantage of the sale. Do settings now carry over when upgrading versions, or did I imagine reaading that? When was that introduced? It has always been annoying to have to redo my settings after an upgrade.
You mentioned replay gain... I don't know if you know it, but MC's replay gain is supported by Squeezebox Server (now LMS), so you don't need external software unless you need it for some other players. I just use MC replaygain, and soundcheck in iTunes for my iPod.
Is your handling of the TrackStat data automated and, if so, how did you do that? I would love to import that data (and my LastFM statistics) to MC.
Yes, it's mostly automated. It's been a while since I set it all up and I dread ever having to set it up again. You need Trackstat and CustomScan for Squeezebox server. You set customscan to export statistics to iTunes. Then there is a Perl script Erland has posted somewhere that runs every night and updates iTunes with the Trackstat stats. Once a week or so, I run MC iTunes Synchronizer to send the stats to MC. I could automate this part, too, but I started having trouble with it running overnight and I just started doing it manually.
A couple times a year, my ratings get messed up and I have to redo them all. I also have my Trackstat stats exported to MusicIP via Customscan, so between Trackstat, Music IP, and iTunes, I can usually get my ratings back by creating a playlist for each rating and updating whichever program is messed up.
Syncing Last.FM stats would be nice, especially now that I am using more music services, but I don't know how to do it.