Having my music organized and mobilized, one more problem to automate. How does one keep track of the music one likes? Move them to a folder/folders, rate them, keep large number of unmanageable play lists over no underlying structure, track the play count. Organizing music on the go is not possible with the iPod Nano. Rating music requires one to be proactive and takes effort. So, I will go with the simplest - tracking the playcount. Now the music you like will have the tendency to float up with a higher playcount. The iPod tracks the playcount just fine. Also, moving among operating systems, installing uninstalling stuff begs for a web solution - a centralized repository to maintain my listening history.
The solution to this one was simpler than I imagined. Last.fm allows for something called "audioscrobbling". You can listen to music using your favorite software and install a pluggin that will upload your "listenings" automatically to last.fm.
Now the problem is to upload the playcount from my iPod to Last.fm. Well, download the last.fm plugin for Rhythmbox and you are set. It seamlessy uploaded the playcounts from my iPod to Last.fm. Just keep listening to your music and occasionally sync your iPod with RhythmBox and Voila your playcounts are updated on Last.fm.
Also, Last.fm has plugins for almost any decent music player under the sun and it can make listening suggestions based on your listening history.