Have Sony improved on their PC-side software since SonicStage and the initial versions of SonyConnect? The software that I used a couple of years ago was so terrible -- even compared to how bad most other software for interfacing with portable devices is -- that it was a complete deal-breaker, despite the decent hardware.

Also, does it play MP3 gaplessly? Sony have long been able to play ATRAC without gaps which is nice, but having to convert all your music to ATRAC isn't so nice, especially when their software doesn't provide a way to batch transcode, except in a way which adds gaps. (Last I tried SonicStage, you'd only get a gapless ATRAC rip if you went from a CD or virtual CD, which made the whole thing a right pain.)

...a Stumbleman, perhaps...?

(BTW - Am I the only person who can't help reading Sony's "Atrac" music format as "EightTrack"?)

Well I read ATRAC as "stay away", but I've only owned one of their ATRAC mini-disk player (the software was indeed very annoying) so maybe I'm not an impartial judge.

Believe it or not, SonicStage has improved considerably over the past couple of years.

Of course, it's still an absolute dog to use and the user interface is so bad that Helen Keller could probably have done better, but at least the version I'm using (4.2-ish) is stable and doesn't have the totally insane check-in/check-out thing that earlier versions had. Version 4.x will do gapless ATRAC rips, at least on my MD player.

FWIW, I have used RealPlayer to transfer stuff to my NetMD minidisc player, but I've no idea whether or not it would work on this particular device - it's far easier to use, and more stable, than ChronicStage, but you will need to download extra drivers from Real to support Sony devices.