SA Footy

I am very much a beginner using this program.
Is there a way so I can multiple songs, one after another, and have the next song fade in, as the last song is fading out, or just start just before the last song finishes??

Any websites that can give me some lessons?

Sorry, never used it. I always use Audacity for music editing.

I'm using Cool Edit 2000 so I don't know if it's the same as Pro or not.
Basically you have your master track open and in a different window the new track you want to mix in. Copy this new track and then 'mix paste' (Edit-Mix Paste) it into the master track. This gives you options about controlling the crossfade & overlap etc.

Hope that helps.