I'm not sure as a mom I would want my caregiver hoofing it across an icy field carrying my daughter because she would get crushed if you fell.

How close to your home/bus stop would you see the boys if they got off ahead of you. Enough they would wait for you to catch up or that you could see them coming to your house as you came up the street the other way.

Would it be possible to get a wagon with wider wheels and drag it through the pathway. I know it would be slower going but still faster than walking around. Also when your own baby comes you would need more than the double stroller anyways.