I pods just don't have the power to drive a good pair of Sennheisers so I'll stick with my Sony MD recorder.
I imagine I'll only use it for the FM feature. Seems convenient not to carry CDs anymore.
Plus, the radio's volume (sorry... "gain" *rolleyes*) in my car is louder than the CD player.
My iPod Photo seems to do a good job driving my Sennheiser 595s..... and I don't need to "up" the volume with them on as I do with my Sony noise cancelling big cans.
The on-the-go removable, replaceable rechargeable battery pack is a major plus on the Sony NW HD5 as compared to the in-built battery of the iPod, which, strictly is a limited-life player, because even though the battery can be replaced, the procedure of removing the battery damages the iPod's acryllic cover . Two or more of these batteries can last an entire trip without recharging. Of course, the iPod's Click-Wheel interface is unbeatable. And I've noticed that the iPod fails to satisfactorily power large headphones, a problem I never face with Sony portables.