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I have an 08 Cayman that came with the base sound system (i.e., front and dash speakers only). I replaced the radio with Pioneer AVIC Z110BT and added rear speakers and the improvement was incredible (and I don't even have a separate amp). The radio offers a graphic equalizer unit and a number of effects that you don't get out of the standard radio, and make a big difference. Adding the rear speakers also helps a lot because otherwise you tend to hear nothing but the engine. It will never be an audiophile stereo without spending thousands more but right now it is very competent.
I had a 99 Boxster before and I hated the sound in that car, too. When I added the factory Boxster rear speakers, it made a huge improvement in the sound in that car as well. Again, not exactly audiophile quality, but then I spent very little $$$ on them. Maybe $200?
So, I would recommend that you replace the head unit and add the Boxster rear speakers, and that should do the trick for you. I didn't replace the front door speakers because: (a) it's a lot of work fitting them, (b) they are matched to the tweeters in the dash, and hence you might need to replace the tweeters as well, (c) the stereo guy thought the speakers sounded okay and didn't try to sell me new ones, and (d) from all I read, the speakers Porsche uses aren't that bad.
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