And one of the biggest came this year when he was surprisingly reunited with an old World War 2 army comrade, Bill Clear, now 96, after the war had separated them for nearly 70 years.
Jock's first big stroke of good fortune came when he, as a member of the British Expeditionary Force, was successfully evacuated with other Allied forces from Dunkirk, France, in May-June 1940, after invading German forces had swept into France. Others were not as lucky: some 11,000 Allied soldiers were killed and about 50,000 taken prisoner.
His second lucky break came much later, a week after the Allied D Day invasion of France in June 1944, during the battle of Villers-Bocage.
Mr Rae was driving a British Sherman tank when he looked up and saw a German Tiger tank heading towards him.
Seconds later, a high-explosive round detonated near the front of his tank, briefly lifting it off the ground. Then an armour-piercing shell went straight through the turret above him, but fortunately did not explode inside.
He scrambled clear via a trapdoor under the tank, avoiding enemy machine gunners.
After that experience, he was sent back to Britain to convalesce.
Before that, he and his close war-time friend Bill had gone through a lot together, both serving in the 5th Royal Horse Artillery, initially in North Africa, then in Italy, and later after the Allied invasion of France.
But when Jock was sent back to Britain, the two men were separated, with Bill remaining in Europe until the end of the war.
Bill subsequently emigrated to New Zealand in 1951, living mostly in Wanganui before moving to Tokoroa a few years ago.
Jock had always wondered what happened to Bill but his only clue, gleaned during a military reunion, was that he might have emigrated to New Zealand.
Later, Jock's son Timothy stepped in and, in a feat of detective work, managed to trace Bill in New Zealand.
Their long friendship is now enjoying a late flowering.
Jock is on his first visit to New Zealand and has been delighted to take up Bill's suggestion to join him for a three-week sight-seeing bus tour around the South Island.
"We can go over all the things that we used to do in the army," Jock said with a smile.
They have just spent a few days together in Dunedin and head to Christchurch today, with another week of the tour to go.
Bill's eyesight and hearing may have been failing somewhat in recent years, but he says it has been "very nice" to see his friend again after all those years.
