I see some old names / faces in this thread, that's great to see! I'm glad the folks from this community are still around to help, the Z group is fantastic!
I might have some unique perspective - I had a few Z's in the past, the most recent was my 1972 shown in my avatar. Around the same time I purchased it, I bought a 1966 Jaguar E-Type, and it needed some work, so the Z had to go. I sold it for $5,000 (!!!), and while I don't regret it, I miss the car. I too have seen the Z car pricing of late, it's both a blessing and a curse. A blessing in the sense that these cars are finally getting their due, but a curse in that I simply won't pay the money people are asking.
Along the way, I purchased a Ferrari 308 QV, which is a real hoot. I love it - it took me YEARS to find one, but I did. I was over on Ferrari Chat (another forum like Classic Z Cars) almost as long as I've been here and it finally happened about 4 years ago.
My point is, patience is a virtue. While a 996 might give you the enjoyment of a modern car (and believe me, don't take that for granted. Even my '84 308 is still "old", and I at times I yearn for a modern classic), there's so much character in these old cars. Yes, they aren't necessarily the best daily drivers. They may be hot, they may smell, they may not be fast, but they are a time machine. I had a Z when I was in high school, and it was the greatest thing in the world to me then. When I had my 240Z, I felt like a kid again.
I pop back in here from time to time, hoping maybe to get lucky and get a nice Z car. Or, maybe I'll sell the Jag or Ferrari and convince the guy in Virginia (Brian??) that has all the awesome Z's and 510's with his dad to sell me one!!!
Good luck either way!!