Ok, so this may have been asked before - feel free to send me to the appropriate thread if so. Searching just got me a bunch of legacy "For Sale" threads. I'm presently leaning heavily on a 5th gen iPod Classic I've modified to incorporate a 128gb MicroSD card. The Wolfson DAC incorporated in its design sounds great and gets me through my work day with a modicum of sanity intact. Thing is, I've been experiencing odd skipping on tracks - i.e. the track plays for two seconds and skips to the next (resolved by hitting the "back" button) - and have been contemplating picking up an iFlash card which allows for the installation of multiple cards (looking for 256gb of storage). Thing is, if I did that (and gave the little thing the battery upgrade it needs), I'm already looking at an outlay of around $150 just for parts - on a player that's ten years old, can't play FLAC and which can't play HD audio... Oh yeah, and which is locked into iTunes. Basically, I'm starting to question the wisdom of investing that much in the player, much as I'm easily seduced by the challenge of "can it be done?" From reading I've done, the 5th gen iPods are reasonably sought after for their DACs and the Fiio DAPs are generally regarded as good but not great. My question is, how does the Fiio stack up against an iPod Classic of that vintage and would I be better off just socking aside some cash and picking up an X1 or and X5? While I have to admit that even the current version of iTunes has an interface I prefer for organization and ease of use to anything else I've tried, I'm willing to leap out of that ecosystem if it is around the same price point and offers a genuine improvement over what I've got now. Any input is appreciated.