[David70]

I have considered a 996 or 997, benefit of the 996 being the cost. My issue with the Cayman is if I buy a used 911 vs. Cayman, keep it for 5 years, not sure the depreciation on the Cayman won't have it cost the same as the 911 and I will wish I had the 911 the whole time.

As said above, you don't say if an automatic/manual or convertible/hardtop is what you want.

I bought my Z4M about 8 years ago, then I did consider a Cayman S as an alternative but for like condition/year the Cayman S was significantly more money, now they have flipped and I think my Z4M is worth more than I paid for it and the Cayman is worth less. Possibly would have been a $15k additional long term cost to get the Cayman.