Couldn’t my iPod read my mind just a little bit?

You really just need to invest some time into using your rating system intelligently. Set up a playlist called "unrated" and go through ten or fifteen random songs from it every once in a while. You'll slowly whittle away at the list. Here's how I use the 5-stars: 0-star: unrated. See above. 1-star: 'delete this song'. Why do I even own this? Delete it next time I'm back at my comp. 2 star: "keep but never hear". This covers things like songs for DJing, specialty stuff, like acappella or acoustic tracks for mixing, or songs that my SO likes but I don't. 3 is okay - I don't mind them on a random mix kind of day. 4 is good - for when I only want quality 5 is perfect, when I want to hear nothing but my favorite songs If you can't file it into a 3,4 or 5, and you have no special reason to keep it, delete the song, already! Life is too short to worry about hoarding songs that you don't even like.

actually, further to this: I do what chrisamiller does with ratings. My most-used playlists are: "Unrated" - anything with zero stars. "picky" - anything with three or more stars, which hasn't been skipped in the last month, or played in the last week "faves" - anything with four or more stars which hasn't been skipped in the last month, or played in the last week "fivestar" - anything with five stars. I only need to rate 9000 more tunes, and then I can start working on genres!

Sort by play count and put the top, say, two hundred most frequently played of those songs in themed lists. Uncheck the rest. Once a week, browse your music and sort/check any music that you miss or that sounds interesting and uncheck music that is irritating you. Rinse, repeat.

Following http://fuzzcat.bactroid.net/2004/07/19/managing-your-ipod-with-smart-playlists/ may help. (That link doesn't want to work for me at the moment, so you can check out Google's cached version http://209.85.165.104/search?q=cache:B5bv3dWfPukJ:fuzzcat.bactroid.net/category/music/+itunes+playlists+absolute+favorites+heavy+rotation&hl=en&ct=clnk&cd=1&client=safari Scroll down to "Managing Your iPod with Smart Playlists.") This method depends on having your tracks rated. For help on that, you may want to check out http://michael.tyson.id.au/software/autorate, which takes a look at your unrated tracks and assigns them a number of stars based on how often the track is played and how often it is skipped. It is not perfect, but it's a start.

Oh, I should have mentioned: I'm on a Windows XP PC

I do exactly what chrisamiller does. (Except I do hoard things in the 2-star category)

In addition to veggieboy's link, here are a http://www.43folders.com/2006/11/10/smart-playlists-for-packrats#besure http://davejay.exit42design.com/entry/All/21/ articles with tips on how to arrange your music. The last one is an interesting way to divide up include the songs you want to hear as percentages of one playlist, including "Old Faves," Newly Added," "Haven't Heard in a While," etc. Invest some time, a weekend maybe, in categorizing your music according to the data that is important to you, and making sure all the other information (genre, titles, ratings) is correct. 1. With regards to your first question, I am the same way. All of my music is labeled under genre (my own definitions) but I have also created my own groupings as well. For example, the genre might be "60s music" but under that umbrella I also have soul, mod, pyschedelic, etc. I use these groupings to create playlists for when I'm in the mood to listen to rock steady one day or french chanson the next versus listening to my entire library on random. My ipod also allows you to listen to songs sorted by genre, which doesn't require a smart playlist — only that the genre field is filled in and arranged to your liking. (I'm not sure if all the ipods do this because my first one didn't, so YMMV.) 2. I have an 8g (older) Nano, and I have way more than 8g worth of music, so I make sure all my smart playlists are limited by, say, 200 songs or 2g worth of tunes. Each of these playlists are also set to play songs least recently heard *or* skipped, so each time I sync, any songs I have been listening to or skipped drop to the bottom of the list and are replaced with fresh songs. Lastly, I download a lot of music from sites like WMFU's Beware of the Blog and sharity blogs. I have one more playlist that is "recently added" songs, most of which are unrated and unorganized. Sometimes, upon further listening, I like the music I download and sometimes I don't. So I also have set time aside every 2 weeks in which I import recently downloaded music into iTunes, sync my iPod, and go through any of the new music I added from the previous two weeks and either delete it if I don't want to keep it or rate and organize it if I do. This rating and "tagging" then ensures those songs get added to the other smart playlists so I can enjoy them when I'm in the mood. I typically don't sync my ipod between these two-week "clean-up" sessions, which ensures that I get two weeks to listen to a particular mix before it changes, and two weeks to evaluate new music before decided what I want to do with it.

Thanks! A lot of good stuff to try here to sort through. That nested playlists link made for an easy and immediate, significant improvement to my party shuffle. Now I will have a party! er...work.