PCDP vs. 5G iPod vs. Karma - what to buy?

hey all - so i have some money to blow and of course i could save though new toys are more fun...but anyway - i have a few options in terms of players:

60GB 5G iPod
Sony DNE900
Rio Karma

for all of these I'm looking to get Senn HD595, a GoVibe amp, and one of RnB's cables

here's my dilemma:

if i went with the CD player, i'd get the MicroDAC too and I kinda want both because I can use the DAC as an external sound card for the computer and such; and the CD Player would make it easier to listen to my whole cd collection without any of that mumbo jumbo computer crap

yet

i kinda want the ipod for convenience sake of carrying all my music around and yes i'd probably resort to lossless for the really good CDs; and being able to watch the occasional video in the palm of my hand is nice - lack of gapless concerns me though

from my research, supposedly the ipod's DAC (the wolfson thing) is great though i donno if the ipod's line out would be the same as from the said CD player through the MicroDAC

in both cases im pretty sure im gonna have a govibe v3 with dual AD825 opamps and then the Sennheiser HD-595

then there's the Rio Karma - only 20GB, but i get the gapless - however i've heard of it's notorious "flimsy" build quality

and i havent bought anything yet, and i have an $800 ceiling spending amount so i could really vary what i buy - i.e. opt for dropping one piece of equipment, getting IEMs, better amp, etc...

so - i would really like some opinions/comments if anyone has any

sorry for the long post

so i think im stuck between the ipod option and the pcdp/MicroDAC option

i figure if i did ipod - it'd be a hell of a lot less to carry whenever i travel, and it'll get a lot more outside of the home use time than the other setup ever will however i wont be carrying the headphones around all the time so the really good headphones will be stuck with the same crappy output from my computer at home - not really that great - but i'll be using the ipod all the time - so should i invest in good earbuds instead? if i went with that option - but i really want the headphones

if i did the pcdp/MicroDAC option - i'll have the reference set at home, still stuck with my minidisc player outside, but i'll have the MicroDAC hooked up to my pc with the amp and my headphones so it'll always sound great - then again how often do i actually sit at home and listen [critically?] to music? - i donno...

so i think the question is really quality (pcdp/MicroDAC) vs. quantity (ipod) and i dont know where i want to be - argh...

though how much does the quality differ? that's probably a good question