Financially, I also can still buy whatever car that I really want and unless you really want more luxury and/or some newer car snob appeal, then I'd say staying with the 986 (and adding whatever upgrades you like) is the best move.
Money is still money and $20,000 for the small list of upgrades for the 987 seems hard to justify as does the $40,000 for the 981. They just aren't THAT much more car for the money as compared to your existing 986.
My greatest temptation isn't a newer Boxster but to move up to a 996 or 997 model. THAT seems to be worth $20K-$50K.
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1999 996 C2 - sold - bought back - sold for more
1997 Spec Boxster BSR #254
1979 911 SC
POC Licensed DE/TT Instructor
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