Before I had a squeezebox, I had a multi-disc CD player from Rotel. And before that I had a single disc NAD player. The jump from the NAD to the Rotel was astounding, simply because of the increase in the amount of music I, and my family , played. If you've decided "I want to sit down and listen to an album," I agree with you that it's no big hassle to put on a CD or an LP. But it's the rest of the time that convenience matters. I know, for example, that when we had a single disc CD player, my wife would NEVER put on music. When we got the multi disc player, my wife would suddenly find it convenient to load up five discs and know there was something good to hear at any time of the day. That meant my children were listening to music throughout the day, and it meant the TV was much less likely to be on at any time of the day.
Moving to the squeezebox has made things that much better. And I don't even bother with the whole play-list creation thing. I just put on an album, and them move around as I see fit. And I get to keep a back-up drive with all my music on it at work, and so have my complete collection of music in both at the office and at home.
The wi-fi issue is potentially valid. I'm now using my squeezebox at home via ethernet cable because I kept getting some pretty obnoxious wireless interference. But most others have little or no problems with that. And I suspect that using a long ethernet cable between PC and music player is less likely to create signal loss or distortion problems than long speaker cables or interconnects.
Only one real problem, as I see it. I now no longer have the liner notes at hand when I want to check up on something that's playing.
Chad