Well, conveniently, I have an iPod classic which has a Voice of the People album on it (Vol 4), checked off as a compilation. It has 2 tracks by Paddy Tunney, and I have another whole album of his on the iPod as well (The Man of Songs). I also have a few tracks of his on The Lark in the Morning compilation album. So I did an experiment for you, and here's a possible solution.

First, do you have Paddy Tunney listed in iTunes as the artist or the album artist? (2 different columns). It looks like only the first item is available for use on the iPod.

I'm asking because I just checked the way I had my Voice of the People album set up. Right now, on iTunes, I have the artist for all tracks listed simply as Voice of the People. Under the album artist column, I have the individual artists listed. (I think the iTunes folks intended this to work the other way around, but by the time I figured that out, I already had several albums set up this way, so I just left it in that format.)

When I search for Paddy Tunney in iTunes, I get a results list with all the tracks on The Man of Songs, and all of his tracks from the 2 compilation albums. But if I search on my iPod classic, I just get the tracks from The Man of Songs, and not from the compilation albums.

So I experimented, and edited one of the Voice of the People tracks in iTunes, by switching the artist and album artist columns. I synced this to the iPod, and searched under Paddy Tunney's name again. This time, 2 albums were listed, The Man of Songs and the Voice of the People album. But only the one VOTP track of his that I had edited showed up, not the other one from that album that I hadn't changed..

So if this is in fact your set up, you should be able to fix it by editing the track information on iTunes. If that's not the issue, then, back to the drawing board!

I guess if you can plan a presentation ahead of time, you could also set up a playlist in iTunes, where you have more searching options, and then transfer it to the iPod already set up with the tracks you want.