Working offshore as I do I have always been looking for quality portables to take away with me to work. To this end I progressed, if that is what you call it, from an iPod Classic through a C4 Colorfly Pro (which I satill have) to a Fiio X3.
This is, by far, the best value for money device I have yet encountered. It plays back every file type I have including my DSD ones and has enough storage for what I want. The sound quality (on Normal equalisation) is better than the Colorfly and this originally retailed at over £500 (£449 now).
I did look at its bigger brother the X5 but thought for the cost difference / features it wasn't really worth the extra outlay.
You could keep the Classic and hook it up to something like the Oppo HA-2 I suppose but this is maybe not the way to go unless you can store DSD / DSF files on the Classic.
Of course if you happen to be loaded you could splash out around £1100 on the latest Sony NW-ZX2 Digital Media Player which is, allegedly m'lud, better than the A&K 120 .......