Bit of a thread resurrection here, but for music I don't think you can beat a used set of decent bookshelf speakers and a cheap used amp. I went from decent Altec-Lansing 5.1 PC speakers to Paradigm Atoms, and the difference is stunning. Might be a little tough to get both for $100, but between craigslist, garage sales and pawnshops it's possible.
Another way to go would be a decent pair of headphones, which I think give better bang-for-buck, price wise. I have Sennheiser 555's (slightly over $100 when on sale), which are amazing for the money. On another thread, someone mentioned getting some refurb'd 'phones for around $65.
Hope this helps.
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