Don't worry about putting allsorts on your iPod, in the past I've had linux working on it, wikipedia, rockbox, etc. It can all be changed or removed if you change your mind and Apple wouldn't know.

oh! i made a big assumption. good to know it doesn't flash anything, makes me feel even safer using it :)

about the power consumption - it is a big issue. at least when playing flac, since the disc access rate increases so much. i basically have to charge it every other day, and i just listen for a few hours during my commute.

http://img217.imageshack.us/img217/9162/22728438.jpg

Lazily

If it's music I made I usually put a date around it so I know what it's about, same goes for pictures

But really..just "X artist - Y album"

Here's a screenshot of my incredibly simplistic process:

http://img519.imageshack.us/img519/9137/stems.jpg

You'll notice that not only do I use a hierarchical structure, but I also still use XP and poor little WMP. I dunno... it plays my music when and how I want it to. I dunno if that's considered "settling" or not. Maybe my expectations are just abnormally low.
Anyway, I've been using this process for years without any issues.
I probably seem outdated and unrefined to most of you, but I'm a man of practicality and I pride myself on it. I know where everything is, and exactly how to use it. I don't lose things and I don't get errors. It just... works.

Anyway, that's me.

I'm afraid posts in the lounge don't add to your post count.

Freebase, do you double click files to play them? If yes, you're a barbarian. :p:

Haha... no.. I right-select a folder to play the whole album, or right-select the band folder to play the whole catalog... Or create a playlist.
I dunno... seems kinda standard to me, barbaric or not. ;)

Like so:

http://img405.imageshack.us/img405/6671/33262969.jpg

All using iTunes.. and of course I have artwork for every single thing

tsk tsk... :D

I actually have a very similar approach. It's just a windows explorer folder like yours, but I have all of my albums in it arranged for example like...

50 Cent - Get Rich or Die Tryin
A.B Cretsil - The Osooku Stars

etc