Let's say you have 1000 folders by artist. You're looking to throw on some random selections but also some specific artist's albums (not an unusual situation).
The way to do it on the iRiver is to scroll through the icon / list view to find the artist, double-click in the folder, find the album and drag it over to the iRiver drive. Then repeat for each other artist's album you wanted to find. Let's say you forgot either the artist or the album name... more hunting. Say you wanted to make sure that the album you chose was the one because you forgot what it was called... so you play it. That involves going into the ambul folder itself, then running winamp or whatever to play the track. The other way to do it is by identifying the tracks you want in Winamp then clicking into your folder heirachy. To select randomly, what you do is to lasoo / control-click the folders and copy them over to the iRiver. You exceed the storage capacity during the copy so you walk out with what you've got. With the iRiver, there's no way to tell what you've played so the next time you just go for pot luck again.
The above doesn't sound too onerous, but the it has caused me numerous minor grief. If you don't own an iPod to compare, this will seem to be one of those minor irritations you work around, like any high-tech product.
In iTunes, I click on the Artist or Album sorting, and it happens immediately. I slide down to lasso the album I want, drag it to the iPod within iTunes itself. If I need to check that the music I selected is really the one I want, that can be done of course within iTunes. Random playlist? The smart playlist takes about 5 seconds to create and I just leave it to populate. Because iTunes / iPod keeps track of music you've heard, you can say don't copy things I've listened to recently.
If your music collection fits on the iHP or if you don't own much music, the drag & drop feature works fine. If it doesn't, then to me at least it's extremely frustrating way to load. Media Center takes away a LOT of that frustration but as a music manager it still lags behind iTunes in speed and usability. And as a tool for loading music onto a player, there is absolutely no doubt that iTunes is better than Explorer.
I know that a lot of these product choices are made on 'what-ifs' by someone who selects one product over another. Having both for an extended period enables you to actually experience the real pros and cons of each product.
With my product designer / audiophile / style guru (you'd be surprised at the kind of people I write for
) hat on, I'm suitably impressed by the iPod as a music player. With my geek / gearhead hat on, I'm suitably impressed by the iRiver as a multifunction audio storage unit. That's really the core difference in my view.