Hello Ryan, thanks so much for the reply!
So, I thought for sure I had previously tried (patiently) waiting for the first song in the playlist to play to see what came next and it always seemed to be the same next song. I had never thought about the 1 or 2 second blank track. Actually it looks like that does work, but it's dependent on the shuffle option being selected in the Audio Playlists window, even if that's closed and you're playing it from a script control. Yes, it does look like that will work for my needs (as long no one has messed with the shuffle option), but it still might be worthwhile to investigate an actual implicit option for this in the script control so it's not tied to the Audio Playlists window setting.
Also, I've just started playing with Playlists, and didn't realize you couldn't reorder songs in a list once you had created it (at least I couldn't find a way). However, using playlists created in Windows Media Player look to be a little more flexible since you can reorder tracks in WMP...and it looks like MediaShout will most of the time pickup changes made in WMP, although it looks like you have to restart MediaShout for it to see any NEW playlist you might create in WMP. Does this sound like expected behavior?