I'm a new Z owner (2 weeks), but I also had a 1995 996. The cars are similar is some respects: Both are high performance/short wheelbase cars that are loud to ride in, and have stiff sport handling.
The age is a huge factor. When stuff starts breaking (and it will), you will pay much more for even minor repair work, even at an independent shop. They figure you have a Porsche, so you can afford it. I also would not touch the 996 without buying an extended warranty, and that will be expensive as well.
In short, I loved my 996, but I'm really glad I don't have it now. The Z? Me like; much, much.
Also, your wife will hate riding in the 996. It's even louder inside than the Z. You'll be in for a lot of "I told you so's," and who needs that?
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