I have this problem, I have 4,000 plus tracks of music and want to get a 16gb iPad. I can tell you it won’t fit there! What if I had lala installed on my server? I could just just use lala.com, check my recent plays list, but then it will interfere with other down load access. I began to think, hey I have this thing the internet, maybe someone has had this problem before. I did some looking and found Sockso, an open source java based music server that gives you search, play list and browsing of your collection. It is simple to setup and use. I had it in place and serving up my collection in 10 minutes. I set up a test at work and forced it to only allow registered users to access my collection.
One of the features I find brilliant is that ability to select how you will play your music. On your local web page you can select from seven different ways to play including a pop-out flash player or a play list download for your default player. Sockso can also change the encoding of your must, if needed.
I think this is the answer to using your music at home, or remotely if you open a path through your firewall, on your iPad or netbook.