I took the 996 out for a drive over the holidays on my favorite short route. For those in the SF Bay area, that's stevens canyon to pierce, up hwy 9, north on skyline, and down page mill. Door to door, less than an hour...very spouse friendly. And when you turn on page mill, you look at the "winding road, next 8 miles" sign
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I did this once in the 996 with a friend driving my old 3.2L Carrera and again in the 914 with a friend driving a 68 911S. My abbreviated thoughts are as follows:
996: I got used to the power after about 1 week of ownership. It is fast, it turns, it has no vices on the road. If you are about the result, you can cover a lot of ground quickly and comfortably here. My friend was working the 3.2L and I was "point & shoot."
I can see why people think the new cars have no soul. They are easy to drive at safe speeds and take a track to push them for the sensation of speed. But they are oh-so-capable. Seriously, there is no amount of money in the world that can make an early car this user friendly and effective.
914: I took this one out for a shake down drive before it goes to its new home. Old school in every way...smells like vinyl and oil, low to the ground and light. Not much in the way of power, but fun to drive at the limit (which is pretty low). Lots of sports car flavor in the 60s/70s sense....low weight, lots of tactile feedback. Fun, but I couldn't really cover much ground without a lot of work. The S was more of the same. Just 200% more intense.
Yes, the old cars have soul (aka quirks) and attainable limits. After about 1 hour, the law of diminishing returns says you want to go home and this has gone from a thrill to a bother (such as when you just want to cover ground quickly to keep the peace).
My assessment: 996 for everyday driving, touring, and tracking. The limits are just too high to be challenging on the street.
Old(er) cars for the thrill, but realistically they are a weekend toy with a finite enjoyment window. Yes, they were built in the day when race cars and road cars were still pretty close. I can get in and feel like Mario Andretti for a while.
Bottom line: all Porsches are thrilling in their own way. What is your kind of fun?