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I'd recommend the 06 280 SLK which can be had new for low 40s, I don't know what you could get an 05 350 SLK for, maybe close to the same, but probably north thereof. You'll get a new car warranty, but most importantly you'll get a hard-top that is an engineering marvel, which would be of value in South Dakota.
The SLK will keep you warmer than any convertible out there with the combination of small cabin/heater/heated seats/airscarf, and I'd imagine that there's some pretty chilly mornings and days in that 8-month driving season you mention. I could run the SLK top-down in temperatures in the low 40s and feel plenty warm. The OEM tires on the SLK are more conducive to driving in sub-50s weather and although I obviously haven't done so, if I had to drive in the snow in either the SLK or the Boxster, my gut feeling tells me the Box would be staying at home.
Keep in mind that the next 3 series convertible from BMW will have a hard-top, but obviously not a roadster and looking down the line a bit.
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05 987 5-speed - Sold
Midnight Blue Metallic / Metropol Blue / Sand Beige
06 MB SLK350- Lease escapee
Iridium Silver Metallic / Black
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