Hi Fi speaker set up from a computer?

I'm a student tired of listening to low fi music, I have a lot of .flac files that I would really like to get the most out of. I have around $250 budget for a speaker set up for my computer (macbook). I was wondering if I got a two channel amp, like a dayton audio t amp, 15 WPC, and a pair of bookshelves to match (don't know what yet), and finally a powered subwoofer, wouldI be able to hook it a up to my computer by (computer)->(amp)->(powered woofer)->(bookshelves)? I listen to a lot of hiphop and a fair amount of jazz, so I really want to have the woofer to cover the bottom end. If you could give any sort of input or info into if this set up would work, it would be great! Thanks for reading my rant and thanks for all input!