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,

I suggest a refurb Sansa Fuse. Often the 8GB can be found for less then $40 and will come with ear buds. The fuse can take a 16GB card, often available for about $20. It will also take a 32GB card but those a very pricey for now. I also have a Sansa Clip+ and it will also take cards. I find both of these devices equal to any Apple product, and of course they are often one third the price.
If you want a portable rig that is going to be on par with your own home rig, you are looking at a bigger investment than $250 for an iPod, IMO, at least if you are coming at it with perfectionist expectations. The big drawback in portable devices is the crappy opamp output. Best to go with a LOD (line out dock) into a portable amp into some fine buds. At the top of that range here's an example of what a great rig would cost:

Classic iPod or iTouch if you want all the added BS $299
ALO Audio LOD $200
RSA SR71B Balanced* Portable Amp $650 OR Triad Audio Lisa III $600
JH16 earbuds $1200
*Whiplash TWAG Recable JH Audio to Balanced $225

Total = @ $ $2300 (welcome to the world of hi-end portable)

On a budget, I've found that my iPhone via UE10Pros is a fine compromise.
My daughter and I share a Cowon iAudio7 and it sounds pretty good depending on the earbuds used (definitely don't used the ones supplied). In general Cowon products have a reputation for good sound. I stay away from the Apple products because I don't want to be locked into iTunes.

Depending on your operating system, you might be able to right-click on the file and edit the tags directly in the properties dialog. There are probably hundreds of free software programs that let you edit the tags on mp3, etc. None that I know of will automatically recognize cuts from an LP (you probably already knew that) so this process is going to be VERY tedious. I've done a couple of LPs and I don't have that kind of patience.

Buconero117 - Thanks - I'll look into it. Price is attractive, as is removable cards.

Jax2 - Thanks for your perspective, I'm going the low cost route for now. If I can't stand the low cost solution I have in mind, I'll save your recommendations and consider them in the future. Can you suggest a similar style setup with outboard amp/dac and earbuds at a lower price point ? Say a $200 amp and $200 earbuds ?

Djohnson54 (Dick) - Operating systems will be windows 7 pro.
I guess I would want to group things into play lists at a minimum and leave whatever 'generic' tags would be in place.
Even though you got some serious replys I would pose the question over on Hed-Fi.org. That is the place where portable audio is a huge area of interest. It competes only with home based headphone audio.
That's actually head-fi.org. Lots of discussion of all of the above, plus tons of used gear for sources, iem's and amps. Good luck.
sorry about miscapitalizing the url but I think they take the caps out anyway. Not the bypass caps.