Hamilton is nice - a short drive to Toronto or Niagara Falls yet still a lot to do in the area. I would advise living on the mountain rather than in Hamilton proper though since you can get the stench of burning steel down there.
Cities I've lived in include Hamilton, Toronto and Gander Newfoundland. Toronto is a great city but taxes are very high (although Canadians in general are taxed to death - about 55 cents of every dollar earned goes to some sort of taxation). You also get some pretty cold weather here. Today the temp was zero fahrenheit with a wind chill of minus 25 fahrenheit.
Gander is an absolute shithole. I wouldn't advise visiting there, let alone living there. Personally I'd rather live in Cincinnati or South Dakota than Gander again. Other places in Canada which are really nice are Calgary, Vancouver, Victoria and Ottawa. I would advise against Montreal, St. John's, Winnipeg or anywhere in Saskatchewan or the other Martime provinces. Halifax is ok I guess.