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Off the top of my head I can think of 2 local 996/986 owners with 19" aftermarket wheels. I have not driven their cars. The tires look like rubber bands or a flat. I have driven Boxsters with factory 18" wheels.
With the lower profile tires the steering inputs are quicker, but in life there is always a trade off. You have more of a selection with 17" tires. If you hit something with 19" wheels then good luck.
We have installed the factory rear speaker kits on about 6 cars. No one yet has yet to asked to install Harvey's kit, which is on your ebay link.
For your year the rear speakers are driven by the head unit. It creates fill sound behind your head.
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