Hi Mark! Welcome to Canada!
From my understanding of what you wrote above, I think the best place for you to move would actually be in Toronto around Yonge between the 401 and Steeles.
Finch and Yonge is a 7km drive from your place of work here, and the area offers a lot more than any area of Markham. The area is called North York City Centre, and is full of bars, restaurants, 2 huge cinemas, gorcery stores and anything you will need. Also, if you wish to go downtown for events, living south of Steeles in Toronto is much easier: the transit is 24/hrs 9vs north of Steeles, which ends wuite early and even then most buses come once every hour, and cost more money).
The area has had a lot of development with highrises, but basically only on Yonge, so the off streets are all older bungalows with large rooms, and a lot of new townhouses have been built on streets like Doris and Kenneth. Living within walking distance of Yonge, South of Steeles will really give you a better quality of life for what you want.