Milton is a mini-Brampton, with a tiny downtown, and no ambition to build upon that. But Milton at least allowed for more diverse housing, much more multifamily including apartments, very different from Brampton where there is
strong opposition against even townhouse developments. And of course there was Brampton's rejection of the Hurontario LRT to its downtown. With the exploding ridership of the Derry buses in Mississauga, I can't help but wonder about the possibility of conversion to light rail one day, and I doubt Milton would reject a Derry LRT into their downtown.
Based on a glance, Okotoks seems more comparable to Bolton, very small and isolated, no real transit system, river through the centre of it. But for such a small place, the way that river divides Okotoks in half is extreme, which will interfere a lot with non-car transportation. The downtown only has one major corridor, east-west only. It's weird that they didn't build a bridge across the river to make the Veteran's Way through downtown their main north-south corridor but instead chose the north-south highway bypassing around the downtown. Milton is actually very different from Okotoks just by being much more cohesive and having a downtown not so isolated. I'm not sure there is another town of 30,000 in Canada so divided like that. Again, lack of ambition.