The problem is, I hate iTunes. I spent about 10 years organizing tracks in windows explorer and playing them with WinAmp. I've always found iTunes slow and the UI terrible. I'm not saying there aren't advantages - I like sorting music by genre, artist, or any other metadata. (On windows explorer, my albums are in subfolders representing the corresponding record label.)
I'm not alone. There is a whole cottage industry of third-party tools to help clean iTunes (TuneUp seems to be one of the better tools, and there are other decent metadata editors like MP3Tag), and people regularly rant about improvements they'd like.
If I want to achieve streaming of my entire library to my home stereo, my best option is to use my iPod touch with the remote application to an Airport Express over wifi.
My Dad had this setup, and it blew me away. He let me connect to his library and stream The Beatles through my parents house. It rocks. I bought an FM streamer to try something similar a few years ago, but the quality was low and I still had to go back to my computer to manage the songs. Being able to walk around with my iPod touch and play DJ is amazing.
I'm hoping that I'll learn to love iTunes after committing to it. It's a necessity now that it's my single music reference for my home. It may even have a couple of side benefits - My iPod touch and car playlists should get cleaned up as well.
I broke down and bought TuneUp. Overall, it's great except for two things:
1. It mangled the metadata on 5 audiobooks (with tonnes of files each), some obscure music, and even some music I bought from iTunes.
2. It doesn't have a feature that automatically cleans all tracks identified as missing metadata. This is a gap, because the 'analyse' feature shows what the problems are.
I upgraded my router to an n-band Cisco / Linksys extended wireless model because my Airport Express would occasionally lose the stream. It's stayed connected since!