Perfectlap, I too would not have purchased a 996 over my 986 even if they were priced roughly the same at the time. I tried both, but my heart was with the 986. I have already indicated that I prefer the design, the handling (which is more precise) and the incredible sound that the driver gets underway because of the side air intake on the driver's side. I remember when the 986 was introduced - I WANTED one badly, but household expenses (and a young son) made it impossible. I loved the 550 influences in the design. I loved everything about it and was even prepared to put up with the relative lack of power. As to the 996 - when it was introduced, I had no similar feelings. It seems that I was not alone fin that regard for, as has been pointed out below, until the upgrades to the 996 in 2002 it was outsold by the Boxster - the only time that has ever happened. And Pothole, I am in complete agreement that for many, the 986 Boxster is an under-appreciated car. I love mine and would not trade it for a 996 of the same vintage.
Pricing? In around 2000 the Boxster started at close to 60K in Canada; due to the improved value of our currency, it remains at roughly the same price today. So yes, I consider the 981 to be 'reasonably' priced for what it offers and a relative bargain. I also suspect that the new 981 Boxster and Cayman may well reverse the trend of 911's outselling the Boxster/Cayman (or at least, dramatically outselling them) since 2001. In spite of Porsche's best efforts to avoid leeching off sales from the 911, I believe that the new Cayman especially will do exactly that; and, I believe that the Boxster will continue to sell in large numbers due to the roadster experience and its lower price. Time will tell.
With reference to future prices, however, the fact that demand was greater for the 2000/2001 Boxster than the same years of 996, bodes well for their ultimate resale value. They were, to many, a more desireable car. The more dramatic depreciation on the early 996 (they started with a significantly higher price), suggests that this remains the same. IMO, that and the new 986 Boxster spec series (which keeps the original Boxster in the public eye), can only help.
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