Not embarrassing at all! And Hangtime is right... the lingo itself can get a bit confusing. Particularly when making a medley, the shifting meanings of "song" and "track" are enough to send a linguist into semiological despair.
Also, ironically, this is the sort of thing that's easier to do in more complicated programs that let you crossfade automatically from one song to the next
on the same track, whereas in Garageband you have to do this manually using separate tracks for each song.
I think I may suspect what you are doing wrong. Did you choose Fade Out from the track menu? If you did, this will apply a fade out to the master track, which means the whole song is faded out rather than just one track. And once the whole song is faded out on the master track, it stays faded out (unless you manually Show the Master Track and fade things back in again).
But for what you're describing, it's not really a universal Master Track kind of fade anyway.
Also... just to be sure (and I apologize if you already knew this), make sure you are not dragging all the songs onto the same track, so that once you fade out the volume to null, it doesn't prevent the next song from being heard. Ideally, you want to place each song on a different track, and adjust the fade outs and ins for each track separately (not universally with the Fade Out command).
For example, say you place song number one on track number one. Say the song ends at measure 60 (or you make it end at 60 because you've had enough of it!). Next, you want to hear song number two begin as song number one ends. Drag song two onto an entirely different track, for example track two underneath track one. It will appear as a new region on track two. Drag the start of this new song (the start of the new region) on track two to around, say, measure 58. That gives you two measures of overlap.
Now you need to adjust the fade out using volume automation, not the universal "Fade Out" command. Click the little disclosure triangle on track one and the horizontal volume automation line should become visible beneath it. Don't be confused by the fact that the line is likely set at 0 dB. That's the normal default volume level, even though it's zero!
Click to add two points on the volume line at measures 58 and 60. Drag the point at measure 60 down to the bottom. The point at 58 anchors the main volume for the whole song up to that point, while the point at measure 60 allows you to fade it out. Therefore, the volume line is horizontal (at 0 dB) for the entire song until measure 58, at which point it angles down precipitously to the dregs of sonic perception.
At the same time, you have the second song (on the second track) starting at measure 58. If you do nothing else, you should hear this song begin at full volume while the first song fades out. However, if you wish to gracefully fade song number two in as song number one disappears into the ether, you need to do the opposite of what you just did with the first song. That is, song number two needs to start all the way at the bottom of the volume automation line, then angle its way up to 0 dB.
Therefore, disclose the volume automation for track two by clicking on its little triangle. Click to add a point right before the song begins (at measure 58), and then click to add another point two or so measures after it starts (at measure 60). Drag the first point down to the very bottom which prevents any sound from being heard, and then drag the second point up to 0 dB. You should now have a fade in for song two.
The volume for song one is at 0 dB until measure 58, at which point it fades down; the volume for song two is null at measure 58 at which point it fades in and up to 0 dB at measure 60.
And voila: the first cross fade.
As you add additional songs on additional tracks, you simply repeat the process: overlap the start of a new song on a new track with the end of the old song on a preexisting track; disclose automation for both and fade out the old as you fade in the new.
When it's time to "share" your song outside of Garageband, the resulting medley will be mixed as one long continuous song. Garageband no longer thinks of each component song as separate songs, but as different musical regions that combine - per your instructions - to create a new song from start to finish.
Good luck and congratulations on your wedding!
