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Use Win 98, for sure!
I midi controller is always a nice thing to have, but maybe it is better to save your money (don't buy the other computer hardware too, your computer is already a very good machine ) and buy a 'beginner' but nice synth, cause than you have a controller too at the same time.
It is just my opnion, a lot of extra memory like 512 do not will improve your system so much, so save the money.
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