You could place many info_teleport_destinations in your map, then set up many trigger_changetargets (one for each destination) that changes the trigger_teleport desitination field to each one of the info_teleport_destinations. Then use a multimanager to fire off each trigger_changetarget in succession. Then have the multimanager target itself at the end, so it just keeps rolling through the destinations. That way the player would be teleported to a different place depending on when he entered the teleport.