it's tough to debate sensibly with apple zealots but lets at least keep a perspective... iTunes has "poor" alot of things. Took to v7 to sniff out and import album art. "compilation" handling is abysmal, too many criticisms to list but it's one strength is enabling newbies to use their ipod AND purchase music.
i use iTunes *only* to sync to my nano but that would be deleted/uninstalled ASAP if i had a different portable player. (i use iTunes to "convert" the .WMA lossless tracks in my main library) down to 128kps AAC for the nano. With the nano you need two libraries if you desire quality music playable on your computer (unless you like low bitrate songs). With WMP you don't (if your player supports WMA) since it will optionally downconvert songs to fit your players memory capacity.
Regarding lossless, I think you have it backwards... AL was a direct response to WMA-lossless based on my knowledge and quick wiki search shows this...
WMA - early 2003
http://en.wikipedia.org/wiki/WMA_Lossless
Apple Lossless - april 2004
http://en.wikipedia.org/wiki/Apple_Lossless
(and you can't get lossless songs from iTunes Store can you).
But lets be honest, ripping down a large library to Apple Lossess would be idiotic given the dearth of compatible products (and mobile phones) that can play them... with or without an apple logo. As PCs migrate into the living room Apple will still be the "mac" (small percent of zealots) and you'll be stuck with a format (apple lossless) that the own company shows no real interest in. Video game consoles & portables won't them... glen