[TSM330i]

Personally, I've always wanted a 911. I had a 2001 Boxster for 3+ years without a single issue and loved that little car.

I'm waiting for my car to hit the magic 8 years old mark before I get my next car. It will be a 911 and more than likely a 997. Which model remains to be seen, but I'm leaning towards either a GT3 or a C2S.
I was "after" a 991 for a while and have read everything I can about them. I would definitely be in for a 991.2 since the upgrades seem to be worth it. Then, I've seen reviews of the 997 vs. the 991.2 and every reason I want a 911 seems to fit with what the 997 has to offer.
A little smaller in size, lighter weight, hydraulic steering, depreciation seems to have slowed dramatically.

That being said, it seems like you're not going to be able to "use" the 911 for what it shines most, it's handling and joy of driving on a windy back road.

If all the roads are straight as an arrow and are in poor condition, I'd go for something that has a huge amount of HP and trades handling for a better ride. It's essentially what you're going to be using the car for.
What that is, I'm not sure. M6 vert?