I own both cars - a 2003 Boxster and a 2001 911 (996). The key to owning a Porsche is to buy something that fits your budget. Budget means price of the car and cost of ownership. The Boxster will cost less to maintain, to insure and repair costs will be less (due to being a newer car with lower mileage and probably not pushed like a 911). Keep in mind that a simple 15,000 mile service at Porsche is about $720. You can find a good independent shop that will do the job for $250. The next service (30,000 miles) is painfully expensive $2,500 at Porsche and $800-$1,200 at an ford vcm 2 independent shop. If you get 18" wheels, the rear tires are 265/35/18 ($300-350 each - tire shops are going to push Porsche N spec tires - they don't want to get sued for selling regular Z rated tires). Fronts are better at $250 ish, again Porsche N spec tires.

The 1999 911 Carrera is a wonderful car. Great handling, steering, power and also a comfortable car to drive ... did I mention power! If you get the 911, make sure its a stick shift. Automatics are very difficult to resell. When you get the feel of the 911, you can drive the car at crazy speeds (tops out near 180). The car rips through corners (you need to keep the throttle down - the weight stays back, which keeps the tires pushed down). If you live in an area with lots of rain/snow, keep the 911 in the garage. The 911 is very rear biased (weight) and the tail gets loose easliy. PSM (stability control) does help, but when you hit a corner hard and the tires give, you'll find it very hard to correct and if you throttle lift, you're in a lot of trouble.

The Boxster is also a wonderful car. It is an incredibly well balanced car, great road feel and steering feedback, has good power and is very comfortable to drive. Trunk space is pretty good, since you have a nice deep front compartment and an ok size rear compartment. You only have two seats though, where the 911 has four (the rears are pretty worthless). Interior is also updated on the Boxster - newer steering Piwis Tester II wheel, stereo, has a glove box (911 doesn't) and feels newer inside. You do lose two gauges on the Boxster, compared to the 911 and the digital speedometer readout is not directly in the center of the dash, like the 911. You get the bonus of a power convertible top. The chassis is rock solid with no cowl shake (the 911 chassis is more solid, but you're comparing a coupe to a convertible). The downfall about a convertible is road noise (even with the top up) and security/vandalism is an issue. The Boxster handles better than the 911 (I've taken corners at speed and the Boxster doesn't get loose). Boxsters top out at 150+, so for most, this is plenty.