What trying to teleport while driving a speedcart did was rotate the player on the mount point to face the teleport direction.
The vehicle did not move with it.
Ive also heard of the setvehicletransform event. I think it was broken due to a blockland update. Either that, or the vehicle events were never that reliable.
As for checkpoints, each time the player would pass one we had a system that would count up adding another checkpoint variable to the player. A player could only get to the next lap by getting all of the checkpoint variables before passing the finish line. Every lap it takes away all checkpoint variables.