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I'll try to answer your questions in the order you stated the best I can
1. The 3.2L is a better mate to the tip tranny since that transmission soaks up hp with it's torque converter and adds about 100lbs to the car. A 2.7L or 2.5L with a tip is pretty underwhelming in terms of straight line accel.
2. I think it is. The best features being the heated rear glass and a glove box for me. You also get a freshened up exterior look and a slight hp boost.
3. The top is very good in the boxster. The earlier boxsters had a one layer top, since about 2000 I believe there are 3 layers that insulate the driver very well and ease of operation is excellent.
4. The boxster is a very good winter driver with a good set of snow tires because of the rear weight bias.
5. I think the hardtop looks great, but I don't have one. That is a subjective issue.
6. Not sure about this one since I've never driven a tip, but I believe the tip doesn't give the driver total control even in manual mode(ie..shifts for you before you bounce the needle off the limiter.)
7. Way old tips were four speeds back in the 993's and 968's ect in the 90's. I believe they have improved them over the years, such as making them "smarter" but no significant changes since the boxster has been out.
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