<< It's certainly not worth $299, I know that much. >>
I have to disagree. I have had mine since it launched and I would pay $299 for it today if I didn't have one. SSX (& SSX Tricky), Tony Hawk 3, Metal Gear Solid 2, Final Fantasy X, Gran Turismo 3, all of the EA Sports games and Grand Theft Auto 3 are reason enough to get it.
The Xbox may have better hardware specs, but until some more decent games come out for it people will continue to buy PS2s.