His older brother, Josiah Gershwin Sing, was a surveyor and he hired William as an assistant for $1 a day. It wasn’t long before William moved into the more lucrative field of real estate. Between 1904 and 1913, Sing bought 22 islands in the area. W. H. Sing’s letterhead gave his address as Meaford, Ontario, “or Pointe au Baril during July and August,” and it advertised “a number of beautiful patented islands for sale in the Pointe au Baril district.”

     Bill Sing wore a peaked yachting cap and a blazer, and he sported a vaguely nautical beard – a costume that conveyed the right combination of dashing elegance and respectful formality to his would-be clients. He loved taking people out in his sailboat, and if it happened that he pointed out an island that was for sale at a particularly attractive price along the way, what harm was there in that? Were he to mention an available property to one of the faithful who gathered at the weekly Sunday services he held at his island, would that be a sin? And if, as it was rumoured, he sometimes confused an outing with an attractive lady interested in viewing properties with the rakish delights of a pleasure cruise, was that not part of Bill Sing’s charm? It is very likely that it was Bill Sing who helped Hamilton Davis pick out the Ojibway Island in 1904 and arranged for his brother Josiah to do the survey of the 42-acre island. 

     Sing employed a local carpenter in 1903 to build a modest cabin for his own use. Its bent-cedar banisters, rough-hewn supports and quaintly rustic bridge were very much in vogue – a fashion emulated by Hamilton Davis when he built the Ojibway Hotel two years later. Bill Sing called his island residence Nugamo – Ojibway for “sing.” However, it was May Bragdon, a friend of the Davis family and an inveterate diarist, who took to calling it “Sing-Sing” – perhaps a gentle dig at the owner’s reputation for sailing a little close to the wind from time to time.

     “Gobble and plunder in Georgian Bay” was the headline of a Parry Sound North Star article in 1910. The selling of crown land by the government was to encourage settlement, not speculation, but this story described an elaborate scheme by which land was being sold to a number of “straw men” – “usually an illiterate working man in the vicinity” – in order to resell the islands, at a tidy profit, to legitimate purchasers. Sing’s name was not mentioned in the article, but it was during this period that he embarked on his “biggest coup in the real-estate line.” Sing sold “parcels” of Pointe au Baril land to Canada’s then-Governor General, Earl Grey, and to several of his friends in England – Lady Beatrice Herbert, Lord Desborough and the Duchess of Portland among them. These properties were never occupied and, in most cases, never even seen by their English owners. The land was bought purely as an investment – one that did not work out as well as the purchasers must have hoped. Some years later, when the biggest piece was sold for default on taxes, it was picked up, at an extremely attractive price – by one William H. Sing.

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