SnooperDuper
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WM started flying with the Wong Brothers at Toronto Island. He was hired by Air Canada when he was 25, so around 1966. He worked for Air Canada for 12 years and Canada 3000 for 5 years, then went into the family business. The seal hunt was in 1981, so I guess it depends whether there were any years between Air Canada and starting with Canada 3000. The business was pretty well done by 1990 and CM was living on the rent from the hangar.
http://www.mississauga.ca/file/COM/9634_MaltonBook_PartThree.pdf
http://news.nationalpost.com/2013/05/31/millard-aviation-business-in-decline-long-before-tim-bosma-murder-suspect-started-to-dismantle-it/
http://news.google.com/newspapers?nid=1946&dat=19810310&id=HYoxAAAAIBAJ&sjid=vKQFAAAAIBAJ&pg=4050,3944726
Very roughly,
Born 1941
1966 age 25 joins Air Canada
1978 age 37 leaves glamour employer and joins discount charter airline Canada 3000
1983 - joins family business, I would say continuing to downtrend
1984 November Della dies
1985 August DM born, barely enough time to make a baby since Della died
1990 - family business basically done
2006 November CM dies
2012 November WM dies
November sure is a sad month for the M family. Seems to me WM might have spent a few decades after the birth of his little prince doing a whole lot of nothing. DM wrote in the obit for WM that WM answered a question with a story, and there may have been a lot of stories of WM working as a pilot but during DM's lifetime, WM was not all that.