Taylor went up the mountain in the cable car late on Sunday, took off his backpack and jumped - arms outstretched.
"A jump that would give him an outer body and mind experience,” a friend said in a social network posting.
On Tuesday, more details emerged that may give an insight into Taylor’s state of mind.
In 2006, he was present when a child, Clinton Aupias, fell from a boat and drowned in Midmar Dam. A friend, Brigette Delport, said this had a deep impact on Taylor.
“He felt responsible for the boy’s death. I think such an incident would have a devastating impact on anyone.
“I met with him after the accident and he was extremely disturbed,” said Delport.
Skydiver
Taylor was a skydiving enthusiast who had bought a farm in Eston and turned it into Angels' Way Skydiving Club.
In 2009 two accidents at Angels' Way within two weeks also disturbed him.
In the first case, a student skydiver sustained second degree electrical burns to her leg, back and arm when her parachute became entangled in power lines after a freefall jump.
In the second, Hymne Cajeux of Durban died after she reportedly activated her parachute too low for it to open properly.
“All these had a terrible impact on Rob. It seems as if he was blaming himself for these tragedies and he was living with guilt and had a huge burden on his shoulders,” said Delport.
A close friend who did not want to be named said: “Rob was a greatly misunderstood person. He ruffled some - in fact many - feathers in our community with the way he did things and bumped heads with many of us old-school skydivers with some stupid stuff that put him and others at risk.
Spiritual person
“He made financial and personal time commitments to aviation that you will never be aware of and aviation in South Africa is poorer at his passing.
"He was a very spiritual person and very few people would understand him,” said the friend.
Another friend commenting on a social network said Taylor was a “big fanatic” of skydiving and base jumps (jumping off mountains or buildings with a parachute).
“So he planned for a year to do this ‘ultimate jump’ off Table Mountain,” wrote the user.
Attempts to get hold of relatives for comment were unsuccessful.