Manually Change Song Position in Playlist?

I know that you can drag and drop songs to re-order them in the playlist, but within iTunes, is there a way to change the song's position in the playlist without drag and drop? If not in iTunes, does anyone know of a third party plugin or program that could do this?
The question seems weird at first so I'll add a little background. I have a playlist with ~1,500 songs in it and I want to quickly change the order of newly added songs to the playlist. Adding a new song to the playlist puts it at the very bottom but I may want to put it in the middle instead and dragging and dropping multiple songs in different spots take a bit of time. Not a huge issue, but it would be cool if there was a workaround

Many Thanks. When I tell you I tried dragging the songs around and "that" sounds fishy, just know that I had to Re-Boot twice just to get iTunes to Open today via Desktop Shortcut. Apparently, my song order attempt coincided with a rare glitch that disappeared.
Thanks again.

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