It's been exactly one month since I started this thread, so I thought I'd provide an update. Thanks in large part to MediaMonkey, I now have achieved in digital audio what I've been searching for about 4 years now. I took my collection of WAV files, placed them into an organized directory structure (very difficult considering most of my collection is classical), converted them to FLAC (the lossless format that I've settled on), and tagged them in a consistent fashion.
The entire is collection on a Linux server, managed by MediaMonkey on a Windows machine. (I also have exported the files as MP3's for use on iTunes on my Mac.) Slimserver software sits on the Linux box, and this drives the Squeezebox (via gigabit ethernet over Cat 6 wire) in my basement that's connected to the stereo.
I have a laptop running Linux that I use preferentially over the Squeezebox's remote control for easier control of playlists and such while I'm listening.
I must say that I'm now thrilled with the results. My music has never been more accessible, and sounds wonderful. Friends who come over are amazed at the power of this system. And frankly, so am I.
Michael