That car should have no problem running 14.0-13.7 @ 98-103ish with a 1.9-2.0 60ft. Unless you car has engine trouble or something; there is no way a 2000 SS automatic with 3.23s should be as slow as 14.3 @ 96 mph just no way(unless of course you can't drive at all or the track just plain sux). My old *** 1995 LT1 Formula with an automatic and 2.73 gears AGAIN 2.73 2.73 2.73 ran 14.4@95mph and that was on the stock OEM tires (trying to remember...225-60r-16 since the car didn't have the performance gears it didn't get the 245-50zr-16 tires) and the rest was completely stock. Now my 1998 Z28 with an auto has the 3.23 gears and it ran a best of 13.9 @99mph and at the time it had a BLOWMASTER muffler and the original owner had backed into something crushing the exhaust tubing(I replaced it with a Borla but never took the car back to the track since our local track sux, it wasn't worth it).
I would think installing 3.73s and shorty headers and pulley would net you a few tenths and a few mph...without a baseline it's hard to say what the mods should give you. But if I were you I wouldn't bother with shorty headers, go with either mid-length or longtube headers. Just remember the 3.73s will make you spin a lot more off the line. If I were you I would get: the mid-length or long-tube headers, a good y-pipe and exhaust, reprogram the PCM(remove torque management mainly and obviously a quality tune), drag radials, SLP CAI (cold air induction kit)brings cold air directly up to the airbox, since the hood is really for looks.