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From an E46 M3 to a Boxster - I'm going to say you want the S.
333 to 250HP is enough of a step down that you would miss it if you went much lower.
I have had brake fade once in my S in 4 track days. This was during session 3 in 100 degree Sun, my first time moving up from the rookie group to a combined intermediate/expert group where passing happened everywhere. I was suddenly NOT SMOOTH on the brakes and it only felt a little spongy. I also had 16 months on the original fluid without a flush.
I tried lots of late braking during my latest track day but my instructor and I were totally unable to get the newly flushed ATE fluid to show any fade.
Despite my horsepower crack at the beginning, I think you will enjoy the switch from M3 to Boxster on the track. The E46 M3 is pleasingly fast but the sensation of speed is pretty subtle. The Boxster yields more awareness of speed, much more direct steering feel and pleasant 'buttometer' feedback. The first few days you will be pleased how the nose points a new direction with minimal hesitation. Once you get used to it, you will be demanding more power again.
Since power upgrades are about as ridiculously expensive in the Boxster as power upgrades to an M3, you might also consider a low priced 2.5L (97-98) Boxster and plan on spending $15K more to add a 3.4L carrera engine and big brakes.
The body is the same in all boxsters and things like unlined top, alarm, keyless remote, etc probably don't mattter so much in a weekend fun/track car as a daily driver. The older Boxsters are experiencing about the same problems (outside of convertible top cables) compared to the newer Boxsters, so they seem to be holding up fairly well.
How did I make up my mind to buy an S? HP and brakes. Since I was buying new, after adding in the options I wanted, the price difference was fairly small.
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