Headed to Ontario, where shall I hit?

YYZ all the way. Get a hotel by the airport, rent a car, and hit some massage parlors and strip clubs. You’ll avoid all the Toronto traffic and it’s easy to get around.

Definitely GTA. Nothing fun in Ottawa that I know of.

For mongering, Toronto (in specific, Mississauga and Etobicoke and similar Western suburbs near-ish the main airport, Lester Pearson YYZ).

For culture and non-mongering, I gotta give a shout out to Ottawa. A delightful city. Wonderful canal ice-skating in the winters, wonderful interstate bicycling in the summers, fried-bread things called "beaver tails" with all sorts of toppings, goddamned tulips everywhere (look up the story), government buildings, major cultural institutions especially national fine-arts museum, tulips, cliff-face over the river for nature parks and mild white-water excursions, mountains and cottages in easy reach, granite and greenery, a couple of large universities and of course all the civil servants so it's a relatively well educated population, and did I mention the tulips? But for strip clubs, Ottawa is marginally lame. I'm sure escorting goes well there, it's tangentially legal in Canada (or, at least, tolerated) and there are all those traveling diplomats so there must be something to that scene, but it doesn't seem to be in nudie bars.