What is a decent first portable player ?

Hello all:
Hope I posted this in the right spot.
This is my first foray into portable audio and I am looking for some different views

I'd like to have a portable system with decent earbuds or headphones for use at work.

Quality does not have to be fantastic just listenable. I'm thinking mp3 at a higher bitrate would be ok. Just the fact that I have music at work is a big plus.

Music taste is about 60% Rock 37% Jazz 3% classical and other

Cost is a factor as well. I could be talked into a $250 ipod if they feel the user interface is superior to anything else.

Currently on the shortlist is a Cowon d2 8gig or similar. Just found one on amazon at $129.00. The fact that has a FM tuner is a big plus as I can record radio programs.

Earbuds would be something from denon or grado.

My wife has a ipod nano I can try - but I have not yet.

So everyone can get an idea my current 2 channel system is:
Basis Debut Table
Parasound belt drive cd transport
Classe DAC-1 D/A converter
Classe Six preamp
Levinson 23.5 power amp
Revel F52 speakers
Stax headphones (tube driven amp but can't recall the model)
Transparent interconnects
Symposium stand (made a HUGE difference)

So, if I want high quality I have the home system. Eventually I would like to get a Alesis Masterlink or similar to start recording my lp's to cd. From there I can rip to mp3 or flac for portable use. ( I think, yes ?)
I'll start by ripping my existing cd's.

Anyone have any other ideas ? Any other portable players and headphones or earbuds they like (comfort and sound wise)?

On a related note:
How would I tag things I record from lp ? What program is good to use ?

Thanks in advance to all who reply,

-John