I, too, have always been a huge Sid Vicious fan. I even criticize him a heap, but only because he didn't deserve certain situations he was placed in. (Such as the Mania VIII Main Event)
I think Sid could more than over-power Kurt Angle, but I don't think Sid has as much chance to win over Angle, as Angle would over Sid. As Shocky said, Angle can take out the legs then work the ground game.. such as he did with Kane, and had great success in doing so.
Vicious will look to use the simplistic power moves that got him far in the business, but as times change, so do advantages and ways to overcome things. Angle isn't from the same era in time Sid was, but if these two were to meet based on both being in their prime, Angle would win due to knowing exactly how to work against Vicious.. whereas Vicious wouldn't know how to counter Angle's speed, yet ability to withstand the power punishment, or constant counters and submissions.
Angle shouldn't have a huge problem with winning, but he'll definitely be worn out before this one's over.