The rates you describe put your husbands time on the road at around 1963, so he was probably much older than he appeared, younger looking from all that cycling. It'd be nice if he could visit at one of our meetings, there aren't many "messenger boys" of that era left alive.
Toronto has a long history of messengers, there is a great deal of it documented here:
MIMA
Some interesting bits:
From
Toronto Messengers - A Brief History by Joe Hendry
"The earliest documented bicycle messenger service in North America dates back to 1880. According to the National Archives of Canada Library, H.T. Baily advertised a bicycle livery and messenger service that was open all night and all day on the streets of Toronto in 1880."
From the
MIMA archives Early Messenger Racing
"Bicycle Briefs
Toronto Star, July 13, 1895
The G.N.W. messengers challenged the C.P.R. messengers to a bicycle race at the island track, any distance to take place within a month"
Another from the MIMA archives;
Early messenger track racing
"Local News in Brief
Messenger Races
Toronto Star, June 4,1896
The G.N.W. Telegraph Company’s messengers intend holding a race meet for the bicycle messengers on the Rosedale Track, Monday June 29th. There will be a one-mile handicap, and three and 5-mile scratch races."
Bike messengers in Toronto declined from the end of the war through the 1960s, in their traditional telegraph boy delivery formats, though they delivered parcels as well throughout their history. In 1979 they reappeared in the current format found in Toronto. The messengers of that time earned $4.00 - $5.00 an hour.