iTunes U order of 'songs' backwards

I just downloaded from iTunes U: "Jazz Insights - Media", a set of programs from Georgia State University. The 240 files were created over a long period of time, from 2009 to 2011. The oldest file was downloaded first, and so on to the end. iTunes 10.4 displayed the files in its iTunes U folder with the newest file on top of the list, and the oldest on the bottom. Trouble is, the program is basically a linear history, and many of the featured musicians are covered in more than one file. For example, the Miles Davis section has 4 parts--4 separate files. Obviously, no one would want to listen to these files 'backwards', with part 4 coming before part 1, but that's how iTunes lists them by default.

I've tried setting iTunes' "Release Date" tab to list the files in the correct order, but regardless of doing this, when dragged onto my iPod they show up listed backwards, with file # 240 at the top of the list. I was careful to drag the individual files, not the folder. And you know, that's not all. Before dragging the files, when they're still in iTunes, many of the multi-part files don't follow each other correctly. You'd expect either 4, 3, 2, 1, or 1, 2, 3, 4, but that's not what we get. For example, Clifford Brown Part 1 & 2 follow each other, but then Cool Jazz Part 1 comes before Clifford Brown Part 3. With Jazz Vocalists you can choose between 1,3,2 or 2,3,1. And so on...

does anyone know, if there's something simple I can do about this? Or do I have to monkey with every file individually? "Info" only shows the year, there are no track numbers, and everything is disc 1.

Thanks,

Greg