I think it is safe to say that this would be a great match! It would clearly go to 3 stages, as ALL matches of this type tend to, advertising a 3 stages of hell match and then booking it to end in 2 falls would be ripping off the paying fan.
Now, both Angle and 'Taker can brawl, but in a street fight I have to go with the Deadman. More sadistic and brutal than Kurt, I could see Undertaker getting the pinfall here, after numerous chair shots, including his trademark guillotine where he crushes Angle's throat on the metal of the chair. A tombstone Piledriver ends this fall. 1-0 Undertaker.
Next is the Cage, and again I feel it is pretty evenly matched. Both men will be hurting by this point, but I can see The Anklelock coming into play here, wearing down Taker's legs and enabling Angle to escape the cage, either through the door or over the top of the cage. This ties things at 1-1.
Finally, the Ladder match. This was a tough one, but Angle in his prime is an Olympic conditioned athlete, and I think he would have the stamina to prevail in the 3rd fall. Taker's legs would be weakened after about 6 Anklelock's, and while both guys would dish out the punishment, the desire of Angle, a man who won the Olympics with a broken freakin' neck, would help him climb to the ladder to meet 'Taker at the top, and knock the Deadman from the top, allowing Angle to take the briefcase.
Winner 2-1 : Kurt Angle