I have been a BMW guy forever, but my last one, the F30 335i, seemed to have lost all of the BMWness I used to love. I like driving fast and handling has always been of utmost importance to me.
My dad has had two Boxsters and loves them, but he also has a massive garage and 3 vehicles to pick from. I like to keep my stable to one car and one or two motorcycles as much as possible. I never thought a Porsche would be a good daily driver. I was wrong.
This thing is so much fun and makes even a boring commute better. The interior is great, I love looking at it and the quality is perfect. I have to force myself to stop looking at the car when I get out so people don't think there is something wrong with me. The handling and the sounds are sublime. Worth. Every. Penny.
If you are on the fence, just do it. I was looking for a 987 for around 30k, but ultimately couldn't justify the older tech and increased maintenance with possible problems when for about 20k more I could have a car that's practically new with significantly better interior. I have always loved the looks of the Cayman. I never thought I would get a 981 but I am very happy I did.
Approximate list of cars for me if you care:
1990 Plymouth Laser (rebadged Mitsubishi Eclipse)
1987 Mazda RX7 (loved that car)
1986 BMW 528e (slow, but it started my love with BMW)
1985 Ford Ranger (unbelievably reliable and bulletproof. I would take one again just to have a beater)
1990 BMW 535i (this thing was a tank and I loved it. I learned so much about cars from this one)
1998 BMW 328i (fantastic car and actually great on the track, but it taught me I can't stand tan interiors)
1998 BMW Z3 2.8 (ultimately too small and that plastic rear window was horrible)
2005 BMW Z4 3.0 (so much fun. I kept this car longer than any other)
2008 Audi S5 (sounded amazing and was fun, but way too heavy)
2015 4Runner (it was nice to be able to drive over whatever I wanted, but it was scary in how poorly it handled)
2013 BMW 335i (probably my most disappointing car purchase)
2014 Porsche Cayman S (all the happiness)