Some ideas I thought up..
Being a bum college student isn't the funnest job around.. sometimes I like to turn Winamp on random and fall asleep.. therein lies the problem of a song that doesn't exactly put you to sleep coming on.. so I thought up three ideas. The first doesn't really have anything to do with the above statement.
The first is just a sleep timer. Very simple, either allow Winamp to play for a certain amount of time and then pause/stop, or just kill winamp.exe, the latter probably being the better choice.
The second is for playlists.. the ability to go in order for an X number amount of songs, then automatically switch to random.
The third idea is probably my most favorite so far, it's a crop filter.. basically, say you want a rock song, go to crop, select new filter, name your filter, and add names to the list.. Winamp will then scan the artist of all the files and remove any that you don't list.. example, you want to go to sleep.. you type in crop, type in sleep mix, add in something like "Norah Jones, Michelle Branch, Sarah McLachlan", etc, you get the point, and it'll crop out every mp3 that isn't by the artist(s) you listed..