Hey Shawn, long time since I've posted something here but...
Caymans (?Caymen?) and Boxsters are surprisingly practical if you don't NEED the back seat and doors - they actually hold quite a bit of luggage/groceries/Costco. And my Carrera has the additional flexibility of carrying 1 adult in the back for short drips when needed.
In my experience owning these Porsches for the last 16+ years the biggest ongoing expenses are depreciation and tires.
If you buy the right ~5 years or more old car, depreciation can be reduced (if a DD) and eliminated (if more occasional use). 987/997 cars are now appreciating and provide a nice balance of modern reliability, performance and convenience while offering the "small" look and feel, NA flat-six motors, and a more raw/less isolated experience compared to the 991/981.
As long as you are running 17-19" wheels and don't need "the best" tires, you can knock the tire cost down quite a bit... although these cars eat rear tires for breakfast, lunch and dinner.
Although there are lots of cars that beat the Porsche sports cars on paper and in stats, IMHO there nothing that combines the performance, driving feel, driving focus, and DD practicality of these cars.
orange260z
2009 Porsche Carrera S Coupe PDK/Sport Chrono Plus - Porsche Racing Green / Sand Beige Full Leather
1999 Miata - Brilliant Black/Tan Leather