I'm considering getting the Soundbooth program because I want to create a track where two of my favorite songs fade in and out of each other in a well-composed way.
Is Soundbooth the program for me? Or is it even possible to do this with two songs I bought off itunes?
You may want to try Audacity, it's multitrack recording software and it's FREE. Soundbooth may not do what you want. I use Audition and it is similar to Audacity and would do what you want but why waste the money.