You are so all over the place that I don't even know where to begin. The Cayman and the GT2 are worlds apart. I have driven the Cayman, Boxter,(when I drove the Boxster is opted not to buy) years later in 2011 I drove 911 C4S, 911 TT and purchased the 911 TTS. Your price range in very wide and I am not saying that these are not good cars but the lower end of the spectrum pales in comparison unless your plan is to build a Moded track monster.

Buy the car that makes you happy and that you can afford. I have wanted this car since I was 17 but I could not affords it until now (44 years old). I did enjoy the trip to the 911 TTS Cab. I enjoyed my Dodge Charger, 300ZX, Supra Turbo, M3, (got Married had Kids Volvo 850 Turbo), Saab 9000 Turbo, Infiniti M35X, another M35X, my DD is a M37X and the 911 TTS cab is my hard earned toy. The only car I owned that I did not enjoy was a 1980 Caddy Seville Desiel. My father purchased it new for my Mother in 1980 and it was a PIG-Slow, Loud and Noisey. She kept getting stuck in the winter until the glow plug issue was resolved. I got it as a consolation prize until the motor blew GM offered him some $ and he got out! My advice is don't buy a car you cannot comfortably afford (pmt, service and insurance), it will eat you up fast and you will not enjoy it. Just my 2 cents.

 

If you don't track your car, then a gt3 is kinda a waste for a DD.
Ck out a gts, very fast and killer deals.

 

Get a 997.1 Turbo. Coils, swaybars and a tune, like stated before.

GT3 isn't as good of a daily compared to the Turbo.