I've got the opportunity to trade my 90k mile 1997 Boxster for a truly awful 1983 911SC Cabriolet...and I'm seriously considering it.
The Boxster is fun to drive and I appreciate the real heat & A/C. However, I don't use it as a DD, and the longer I have it, the less it's worth. The larger issue is, though, that compared to the 911s I've owned ('67, '72, '84 Carrera and a '76 912E if that counts) the Boxster somehow feels less special, more like 'just a car.'
I had no plans to sell the Boxster at all, but this really ratty 1983 911SC Cabriolet with a horrendous Strossek-style fiberglass body kit found me. Part of me really wants to 'save' that old 911 and to return it to the stock bodywork.
Boxster pros: real heat + a/c, can use as DD if desired, doesn't beat the crap out of me on long trips, wifey likes it, if I want to HPDE all I need is a factory hardtop. Easier for me, as an amateur, to drive quickly and autocross. It won't rust.
Boxster cons: I hate OBD II, it's red, and the refinement I enjoy is also what makes it a little antiseptic compared to an old 911. It's still depreciating.
911 pros: CHEAP!, black/black/black (my favorite), that incredible sound 911s make, the telepathic steering, and that sound. No rust. Everything I do to fix it up and/or return it to stock will increase it's value.
911 cons: it's a convertible so no HPDE, feeble heat, no A/C, wifey won't ride in it, crappy shifter, high mileage, this particular one needs LOTS of bodywork to be put back to stock and has cheap all-vinyl 924 seats in it.
I know the obvious answers are
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sell the Boxster and get a nicer 911 than the one offered to me. Can't do that for a lot of reasons (it's personal).
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Miata.
So, what sayeth you wise GRM readers?