What is a useful program for creating a digital mix tape?

Honestly…itunes works wonders. If you go into your settings you can set it to crossfade, leave seconds between songs, etc. I make all my mixtapes via itunes and they’ve all come out great!

@adreamofautumn That’s a thought :) I’ll consider it, but I’d like to find something that gives me a bit more control over what I’m doing. I’m a graphic designer by trade so I’m a control freak with this kind of thing.

I actually did an entire episode of my video show on sharing music and making digital mix tapes. This is all done on the web, and I’m not sure if that’s the solution you were looking for but there are some cool sites here.
http://thewebmix.com/2009/02/04/show15/

Not bad here.

@TheWebMix Thanks for the resource, but I would like to keep my mix off the web.

@vindice Thanks; that software is the sort of thing I am looking for. Unfortunately the application is 50 dollars and for Windows only. If I can’t find a Mac solution, I’ll have to cave and boot up my PC.

iTunes Genius.

Audacity