I'd vote for spending $2500 on headers, intake, ecu reprogram and spend the second $2500 on going to the race track.
Track equipment runs about $800-$1000 for BK rollbar extension($500 used), 2 harnesses, and a mounted fire extinguisher. This leaves about $1500 for 10 track days at about $150 each (assuming you don't need a hotel).
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changing my advice - If you have a lot of weekends without commitments (Mom's car sound like you might be free of wife and kids), I'd spend the whole money at the race track. Forget the 'schools' for now and go out with Porsche Club of America, NASA, etc.
The base boxster goes over 150mph, which is probably enough top speed for the first year. The acceleration of 6.x seconds to 60MPH is respectable. Until you are ready to spend $40,000 in upgrades you won't be able to take a Viper, or a Z06, or an M3, or a Porsche Turbo, so resign yourself to being faster than 99% of the cars on the road and enjoy the exhaust note of the other 1%. Then with your 10 days at the track, you will KICK THIER ASS on a mountain road. Believe me, just riding on the tail of a 996 twin turbo along a curvy mountain road is fun for you and humiliating for them (and I only have 5.5 track days).
If I were you, I'd live with the car for a few months and a couple of days on the track. After 2 days on the track you will know if you need to be faster in top speed(yeah right), faster to the next stop light(new car), or just quicker in the corners(upgraded suspension).
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