Okay well... I'm not sure how Ipads work, but... here we go, I will try to explain.

You should have a folder that contains all of your music for your Ipad right? If not, is there anyway to create a new folder and move the music onto your computer?

Once you've done that, and your Zune software is installed, there should be some 'settings' on the Zune program that allows you to select music from a certain destination/folder.

Should be under Settings - Collection. You'll see a 'Music' area, you click manage, and I think that is how it's done.

It's been so long though... maybe it's still how you do it.

Hope this helps if this is still how it's done. =]

I'm not really sure on that one, might check this out though.