I finally was able to figure out a way to get iTunes to make a playlist based off of how much I listen to a song in a day. I asked about it on the apple forums about a month ago and no one was able to help so I played around with it a bit tonight and got it.

Plays per day

I really really like the playlists that this makes. Its like a most played except the value of songs decay the longer they are in your library. It fixes the problem with Play Count which tends to favor songs that have been in your library longer. I recommend to filter out music that has been added in the last month since those songs seem to get an unfair advantage as well.

One thing I didn't mention on the forum post is that I did have issues with the comment field on some of my songs. They had returns on them and were throwing off values, so I went in and either removed the return or in most cases just removed the comment entirely. This was mostly on older #anime-ongaku releases.

Oh, and if you're curious what I've been listening to lately, here's the list I came up with.