Damn, I'm late to a Sqeezebox discussion but I'm glad to see all your questions getting answered. Stupid vacations. Umm Wait!!
Mike, I never have to reboot my SB server either. If I do, it's likely I did something experimental stupid and had to reboot the whole PC. My Classic player does require a manual reconnect after a power bump though. No biggie though, just keep hitting the right arrow button on the remote a few times until it reconnects.
I'm pretty meticulous with my tags but I still find discrepancies now and then. "MP3Tag" is a great tool for identifying and fixing discrepancies. It will let you view as many folders and subfolders together as you want so you can do mass changes where you have made a mistake just for certain albums.
For instance, you notice you have two Artist listings for "The Tragically Hip" because you forgot the "The" for a single album when you ripped it. Choose your "The Tragically Hip" folder and you will also see all sub-folders. You could visually scan for the discrepancy and fix but just highlight them all, re-enter the band name and then all albums are now automatically now the same.
Then you can automatically, in one step, rename all of the file names with the new, proper artist name so they will be fixed as well.
It also allows you to save multiple default file naming creation styles so you can name your files differently for classical, for instance.
It also let me add new tags for things like Composer which also helped me to better organize classical which gets much more complex.
