On your other complaints about the iPod/iTunes (1,2,3,4), you make a convincing case. I think with your requirements in the last paragraph, you’ve rightly assessed that the iPod and iTunes is not for you.
But point 5 (“requires custom software”) lacks your usual clarity. Don’t you want to manage your music at a higher level of abstraction than files and folders? Even you agree, as shown in “Trees, TreeViews, and UI” ( http://www.codinghorror.com/blog/archives/000246.html ):
"I’ve aggressively adopted the label approach, because it’s so much more reflective of the fluid way things are organized in the real world. Programmers may love rigidity-- to each item its appropriate folder and meticulously named class hierarchy-- but users prefer simple, flat lists. "
Could it be perhaps we are still stuck with the filesystem concept? I beleive you were talking about the length of an absolute path file name on Windows last week (excellent article, BTW).
This is what the iTunes application does. It provides more functionality that the filesystem. It has static (ID3 tags) and dynamic (your rating, play time, play count, playlist, playlist membership, etc) attributes. It can display arbitrary selections using those attributes into simple lists (Smart Playlists). It can automatically sync music and video based on those attributes. You can data-mine your own usage because the iPod records usage data.
With that I don’t see how iTunes can be compared to your 3 step drag and drop. Like James Randall said:
- Plug in the USB cable
- Disconnect the USB cable and rock
- (There is no step 3, even on a Windows!)
Then again it seems like you don’t require that type of usage.
With that said, iTunes is like the running back that stopped on the 50 yard line. So many programmatic things left untouched (no programmatic way to create SmartPlaylists, SmartPlaylists query language is 70% good enough, etc), so many implemenation flaws (auto-syncing only occurs on insertion and does not auto-sync new music added while iPod is connected, heavy CPU load, etc), and strategic design decisions like no WMA/OGG, iTunes store.
Oh and please correct the external hard drive comment. You obviously need to update your info on that.