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I haven't seen a bad review of the Macan and while I haven't driven one, they are absolutely beautiful and comfortable based on my brief time in one at a Porsche showroom. If you can make it work, get it. Reviews certainly favour the Macan over the Cayenne. Little smaller, more nimble, quicker, yet just as comfy and awesome.
Maybe you could get a nice package deal. Trade in the 996 and the two Boxes and get a Macan and an 09+ Box (or sell all privately to max out your return). You could probably do away with the truck with a trailer added on, although trucks can be pretty handy.
Anyways, that's my .02 cents. I'm not worried about the Macan's history. Lots of new cars have been rolled out and have not had a bit of trouble.
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2011 Boxster 987.2 Arctic silver / Black leather, PDK with Sports Chrono Package Plus
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