Maybe try a different player maybe something like Winamp ?

http://www.winamp.com/

Edit: Looks like Winamp is in ownership transition and only older versions can be downloaded. So may not really be a viable choice.

http://forums.winamp.com/showthread.php?t=374929

Granted it's been quite a while since I used it but it always seemed to perform well. Had an equalizer and I think if tied to internet access you could download an add on for Leo's Lyrics that brought up all the lyrics as the songs were played. 

Myself I still use the FM transmitter plugged into a 12v lighter socket with a USB stick in it.

Plays in the  pickup truck almost continuously and shop radio can usually pick it up.

Not the highest quality audio but generally not important as there is other noise anyhow.

Only drawback is lack of ability to sort songs into deeper folder hierarchies and the ability to skip quickly to a particular song in the order of things.

I can't listen to regular radio anymore too much chatter and too many annoying commercials over and over and over.

All I want to hear is selections of tunes of MY choosing. Mosty 80's rock music with a few other things scattered in between.

Also great for listening to podcasts on many interesting topics that you can download. Again however very tough to sort out specific ones with my device set up. Would be much easier with your laptop setup. 

Slightly off topic how are the VR3 radio receivers that accept USB flash drives and play mp3's holding up in the tractor applications  ?