If I remember correctly, cafepress has a CD service where you upload the content you want on the disk, design your cover and insert, (maybe label too?) and they handle the rest, shipping & all. Might be something to consider if it's cost effective.
This idea reminds me of a lot of the computer magazines that include a CD every month of all kinds of freeware & trials of various programs.
Now I am not saying that we should do a new CD each month, because that would be crazy, but maybe for the beginning of 2007 we could release a DC Best of the Year disk with stuff from the previous year in the way of software trials and DC programs. (Limited edition collectors disk)
That would be plenty of time to get permission for distribution of the trial versions and put together a nice collection.
And we'd have an entire year to decide what will go on the 2008 CD.