Hi.
I haven't got a *huge* amount of experience with this either, having
done it for the first time a few weeks ago, but I *did* manage to
reorder the playlist with drag and drop.
Let me first say that this is under leopard, so if you're using tiger
it's not helpful.
It's true that, when we use drag and drop with itunes it duplicates
the song, so it's not perfect, but it's a bit less tedious that the
previous two options.
Basically what it involves is intereacting with the outline for the
playlist, go to the song you want to move. make sure your mouse is on
that song.
Use the drag command on it and move to where you want it and drop. I
can't remember now whether when you drop the duplicate appears before
or after the song you're on, but it shouldn't take much playing to
work it out. Make sure you check the mouse is where you think it is
before you drop, since that can be a bit strange occasionally.
What you've got now is two copies of the song, one where you moved it,
and one where it was originally. Just go back and delete the first one.
As I said, not perfect, but it does work.