Turns out God kinda likes me, as I found that I have an unopened iPod gen 5.5 in my house that I was not aware of!
So for now I'm deciding not to iMod it because I'm not crazy about the idea that I can only play music through one of ALO's cost-of-a-kidney cords and not through a low-profile LOD or a dock or anything. I may change my mind later, but for now I think I'm going to keep it as an iPod and just throw a 240g HD in it.
That being said, I'm sure this has been asked several times, and I've been browsing the forums for a while trying to find something more specific to my question, but all the threads kind of went off topic.
Is the 5.5 still the best sounding iPod? Or does another flavor of iPod surpass it now?