healthy single person with no family responsibilities
^ You've just described (conservatively) over 50% of area's demographic. The same people that get into their cars every morning to get downtown, suffer through traffic and pay unholy amounts of money for parking there, and then complain about lack of proper public transit in the area. Some don't embrace the cars. They suffer through 1++ hour commutes to downtown by 501 streetcar that is crammed like a sardine can most of the way there and back. These people actually have the right to complain about the lack of proper transit connections. And somehow, none of these people realize that their commute would be faster, cheaper and more rewarding if they just use the bike trail. As I said, if you are absolutely allergic to sweating, there are e-bikes out there. There are a couple of guys using their e-bikes on the trail every day. They cannot be accused of being fit. But they leave me and all other cyclists in the dust with their speedy electric powered machines. Judging by the speed difference, I can't imagine it would take them more than 20 minutes to get from HBS to Union. After that, the subway is your oyster, go anywhere in the core quickly and conveniently. All I am saying is: a fast, easy, convenient and affordable option to commute downtown is there. It satisfies the vast majority of HBS demographics. Yet, so far, people prefer to moan and complain about sitting in traffic for an hour every morning instead of using the actual rapid commute option that is right there beside their vehicle that is stuck in traffic.
Moreover, if you have a family, I'm not sure how transit connections to downtown would improve your living situation in that regard. You will still need a car to drive your child to Montessori/school/pool/hockey practice. All I am saying is: this area is absolutely great for people who are not religiously attached to their vehicles and are willing to take advantage of the great bike trail commuting options HBS has to offer. For everyone else, there is MasterCard and a nice subdivision somewhere in Pickering.
roblem of course is once you leave the sanctuary of the Martin-Goodman trail
True that. In-town cycling can be gnarly. And definitely not possible year-round. I am lucky enough to work in SoCo, so 98% of my commuting distance is covered by the trail. However, see my reply to
@AHK regarding commuting by the trail to Union. If I worked somewhere in-town, say Yonge/Bloor, I would do just that: cycle to Union (which means you are off the roads for the vast majority of the way) and then catch the subway uptown. It would still be faster than trying to get there by transit alone or by car.