If you manage your music in iTunes already, another option ya'll might want to consider is a small app called
iTunes Export by Eric Daugherty . This solved my problem for exporting playlists (and the music files with them) to my EVO. I've used iTunes for quite a while to sync my wife's and daughter's iPods. Also use it to manage apps on an iPod Touch. I didn't want to use another music management app like WMP or DT just for my EVO.
The iTunes Export app allows me to continue managing all my music in iTunes and when I'm done adding music or editing playlists, I simply hook up my EVO (disk drive mode), open the iTunes Export app, configure the settings (including export location of EVO music folder), and run it. It converts my iTunes stuff to my EVO easily. It copied album art as well. After it transfers to my EVO, it takes a little bit for the music app on the EVO to sort through everything but in just a few minutes, my playlists showed up and I'm in business. Short of native integration with iTunes (which will never happen), this is exactly what I was looking for. Something simple I can run to move music to the EVO from iTunes.
I did have to use the older version of the app, however, as my PC had problems installing Adobe Air which is required for the latest version of the iTunes Export app. There is a link from the site to the previous version. I highly recommend IF you are committed to iTunes.