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I'm lucky enough to have owned a lot of cars including (pertinent to this discussion)
- 2001 S2000
- 2002 S2000
- 1997 NSX
- 2008 911 Carrera S
Each of those was sold for the next one as my fun, third car. I just bought a 2008 E90 6 speed (in my case, the birth of a child necessitated a real back seat to get car seat in/out).
I agree with a lot of your comments about the relative merits of both vehicles and in a vacuum would think that in most respects, the M3 would be a better only car for your situation than the S2K is. However, given your comments about finances, etc. I'm going to agree with mlambert890 and suggest that you strongly consider keeping the S2000 and purchase a cheap, used, late model Japanese sedan/wagon/SUV (Subaru Outback, Honda CRV, Toyota RAV4) to rely on as a DD and for the HD runs you want to make.
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