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I bought a 1987 911 coupe last summer, a couple of weeks after my dad bought a 1999 Boxster. The cars are totally different. The Boxster feels like a modern car, whereas the 911 feels like it's from another era, which I guess it was.
But ask both of us which one we prefer, and we'd both say the 911. There's just something about an air-cooled Porsche 911 that is just very appealing, from the smell of oil to the stiff clutch to the various creaks and groans in a 25+ year old car.
The 915 vs G50 transmission difference is real. Having driven a number of 911s during my search, the 915 transmission can be very vague compared to the G50. However, I believe 915 transmissions can be fixed/adjusted to be very smooth, and with experience can be just as easy to use.
As others have noted, the major expenses are engine and transmission rebuilds. If this one already has had that work done, then it should be good for another 50-75k miles.
I would definitely buy it, you won't regret it.
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