Geeze, if you want me to come back I'll do. You are in the middle of an MP3 player recommendation thread, trying to convince someone else than the OP that no music management software is better than one. Apple could be out of the equation but you compare everything in your perfect management method to the Evil Empire of Steve Jobs.
I'm sorry you think I'm trying to convince you or anybody else that one thing is inherently better. What I'm attempting to do is to simply illustrate there are (better, IMHO) alternatives out there. Whether or not you agree they are is entirely up to you, but my main beef is to judge a given product without having tried it first. For instance, if you would tell me "I've tried a couple of Cowon music players and didn't like the sound" I could respect that, but as it stands, it seems most people are afraid of delving into anything else but iPods. They're comfortable with what they know and fear the unknown.
From what I understand, most online websites in the US will offer refunds for products that are ordered and end up being returned because they aren't fully appreciated. I'd suggest taking advantage of such a policy as opposed to potentially settling for nothing else but mediocrity. What if you enjoy the Cowon (or any other manufacturer's product) better? You'd be thrilled you decided to give it a try. But most people will forego giving a competing product a fair shake because of the lack of the fruity logo on the back.
Thunderscreech mentions that he'd probably use iTunes, as it's easier for him. I started from that point, knowing that you can drag-and-drop elements from your iTunes library to any MP3 player that works as an external drive, which you apparently did not.
There are alternatives to iTunes that will auto-organize people's music library. For instance, JetAudio 8 (Cowon's free offering) works great. Personally, I like it better for a few reasons. It also offers sync options as well. However, day-to-day, I don't use an application like this. Simply dragging & dropping files is all I need & want. JA8's main use for me is to toy with the ID3 tags.
But there are numerous other applications that'll do as good a job and are more responsive than iTunes. I didn't try them all, but did appreciate the fact that there are choices out there. However, in the end, it's what you're most comfortable with. But if you find you like iTunes more after having tested some other options, more power to you.
For the record, I own 2 iPhones (3G & 4) hence why I have experience with iTunes... and why I despise it so much. Some people love it, others hate it. We all have our reasons.
Before doubting my ears' ability to hear the vast improvement in sound between two products however, I'd strongly suggest giving a Cowon product a listen and configuring the EQ to your liking. I'd be curious to hear what you have to say afterward.