Earphones are a HUGE difference.
I have used a variety of players with a variety of headphones, budphones, everything. The player can only do so much. Imagine a high end amplifier in your lounge with some $50 speakers? It wouldn't do it justice - in fact - it would make it sound worse than a crappy amp with the same speakers.
First thing I do when I have an mp3 player is get good budphones. I spend around $50 on them to get something that will last, not fall apart and have excellent quality.
I bought an iRiver H320 around ... I don't know, 6 years ago? $600 it cost me. At the time though, it was MAD. 20 Gig HDD sold me easily enough, and the fact I just plugged it in to the PC and dragged music (And whatever else) to it. I could use Winamp playlists as well, so I could generate playlists on my PC and copy them to the iRiver. I still use the damn thing, and I have no doubt better cheaper larger devices have come along - but I love my H320

Plus, firmware updates later on made it possible to watch video on them too - excellent for the bus.
iTunes.This has become better over recent releases. For 90% of it's life it's been bloated over-hyped trash. I've never seen such a resource-hungry media player/organiser on a computer. It looked "ok", but fell over in many ways, mainly due IMHO to it being a product of Apple - where you take out EVERY feature and add in some basic things of what people might want (single mouse button anyone?)
But recently, it has become more streamlined. I have had to setup iTunes for various people, older, younger, who have falledn into the iPod trap - and it isn't as bad as it used to be.
I do wonder though, how it can be SO easy to somehow "lose" your music by clicking one wrong button? Seems silly.
The biggest aspect I like of iTunes is the visual display of albums - with the nice slide effect. That's what I want in my lounge in the end, a screen that is touch-sensitive, where people can flick through a virtual jukebox using their pointy.
That layout though, isn't conducive to people who have more singles than albums, or just some songs from an artist - creates a bit of a flawed perspective as to what can be played. Why have the album cover for an album if you have one song?
there are a plethora of other media players/organisers out there, just go and search. SO MANY of them have iPod plugins as well, so that you can use them to create playlists and synchronise your music. Even Winamp can do this. Check out Winamp, or MediaMonkey, or FooBar or various others I can't remember off the top of my head.
I have a server at home, sitting there with amongst other things, music on it. It's a NAS unit, effectively. Network Attached Storage. About the size of a small toaster it has two 1TB drives in it, mirrored. This means that I only have 1TB of storage but when data is written to one drive, it's written to the other. Redundancy.
Because this device is on the network, I can access it from my PC, my laptop, my original Xbox with XBMC installer, and the Phillips Stremium I have in the bedroom. Music anywhere, from one source. That's what I wanted.
At one point I also had speakers outside, linked through wires to the PC inside.. and some software on the PC that allowed me to access Winamp with my Mobile Phone. I could change song, change volume, reshuffle, pause, stop, whatever, all from the number son my phone. Fun.
Sorry, I just wrote soo much so I'll stop now

I don't mind if people like iPods, and iTunes. I just detest "iPod" being used as a generic term for an mp3 player in general.
Call cling wrap glad wrap (tm) all you want. Call a pen a Biro (tm) too.. just don't call an mp3 player an iPod.