Audible.com is evil.

I spent 3 hours last night getting my old Diamond Rio 500 working for my wife to use. She likes books on tape, so I thought to myself "self, I think the rio 500 is compatible with Audible." I also remember thinking that the audible.com software sucked when I got the rio in 1999, so, maybe it's better now.

Nope.

You have to be an adminstrator to use it, not just to install it. If you're not, it fails in misleading or silent ways.

You can't have an adminstrator install it and then have a non-administrator use it. It fails in silent or misleading ways. The audible.com FAQ on this starts out with "fire up regedit".

It's evil.

If protected audio is going to be this hard, the RIAA has a lot to worry about.