If you're using earbuds, I'd say stick to your iPod . Jk Jk...I see your sig and see what you have. Although I'm not familiar with most despite owning 2 of them but a long while back.
It's funny that you ask this today 'cos when I met up with a couple of Tokyo Head-fiers today, we agreed that really it's the headphone/earphone that defines primary (or biggest) signature & quality, thereafter the DAC, then amp. The cables started to get somewhat blur (as to whether the ear/headphone cable vs backend ICs vs power cables, etc.). Despite the topic being more about desktop setup, I think in part at least it's applicable to portable.
So my personal 2 yen worth is that if you have a pair of headphones that hasn't reached its full potential yet, then that's where the DAC, then/and amp come in to give that extra edge. On the other hand if the ear/headphones has already reached its full potential with your iPod video+cMoy BB amp setup, then going for a higher end DAP may see little rewards.
We did discuss about track quality too and we agreed that the difference between 256k lossy is probably the "best bang for buck" and for most of the tracks it's hard to tell the difference (or at least to satisfaction) in comparison to 16/44.1 lossless. I think I'd be even hard pressed to find 4 out of 100 of my best tracks to be able to tell if it was 256k lossy or lossless (but I do have 7214 tracks) and even for those I can tell a difference, I would have to listen pretty hard to tell the difference - in which case I'm no longer listening to music but just listening to detail and nitpicking. In other words, I'd still at least enjoy the music even at lossy. 128kBps on the other hand is a completely different matter.
Personally for me, I feel that the h/w component changes (DAC, Amp, cables) would make a bigger difference than 256kbps vs lossless.
This is just my personal beliefs which I've shared and agreed with some other Tokyo head-fiers.
P.S. no joke, earwax could potentially affect more than lossy vs lossless!
Well for the tracks I know intimately, I can definitely hear a difference between lossy and lossless. That being said, however I am not able to tell between lossless vs another lossless codex. For lossy codex aac 256 still betters mp3 320.
The rest of the sentiment, however is spot on. The right set of cans means everything. The rest of the gear makes minimal differences.
For me +/-20 hour playback + flac + expandable memory = win.
This is from the guy still using the 1st gen ipod touch and ipod 5.5 (non modded)