There's a flaw in your logic here -- you don't need to use iTunes to get music on and off. I'm a big fan of free and lightweight, so I've begun doing the rounds with some of the alternatives. Yamipod is good if you just want to get your music on and off and don't care that much about syncing, while ephpod tries to be more of an iTunes replacement. I've had the iPod plugin for Winamp for a while to handle my Shuffle needs, and I've been highly impressed with it, but I have yet to try it with the iPod itself.
And as for the power cable, I feel your pain. I just paid $30 for a non-OEM charger and cord before discovering that eBay had them for basically shipping charges. But there's really no other alternative, at this point, and the cord is *not* that big. My external hard drive cord is lots bigger.
I don't see what is wrong with using software to move tracks from your HD to your iPod. Actually, you know - it's quite useful because you can sort/choose when tracks start/convert and so on.
What I would say is ****ed up is that the battery is crap. The irony of having an iPod video because you can't watch a video that's like just about 2 hours long, unless you have the backlight off and never touch the buttons/clickwheel. Btw, you can barely see the screen with the light off but Apple don't care about that. They only care about how long they can make the battery last using most efficiency.
You've missed out many things about the iPod which are bad. Like, you can't play many games on the iPod unless you have a linux. You still have to buy so much more for your iPod if you want it to perform better. I felt the iPod should have came with a DAB digital radio, especially the 5G for it's price.
I do use my iPod all the time though and it is useful.
I just know not to trust Apple ever again.