In terms of urban design, Markham might be a poster child for trying too hard, yet not hard enough. At least in a piecemeal fashion. They are putting in transitways and new urbanist developments wherever they can, but they don't work together. The transitway through "Downtown Markham" works out to be slower than if it just stayed on the main roads, and many such developments are constructed away from these roads as well. Even the "model" NU development of Cornell is just a subdivision with a retail building in the middle!
This is reflected in the transit schedules in Markham. Despite this desire for post modern urbanism, they cannot seem to capture the soul of it. Compare this to Richmond Hill, which at least along the Yonge corridor south of 19th, there are mixes of uses right along the street, moderately sized parking lots, and several high density developments going in as well. It might not capture the form, but it does capture the spirit. Even streets like Major Mackenzie, 16th, and mid block north-south routes are seeing increasing ridership and/or frequencies.