>Americans just in general tend to drive their kids to school dues to fear of child abductions and related ever-present paranoia.
This is really just an upper middle class thing.
>The street organization is irrational, derived haphazardly from ad-hoc pre-auto paths. The public transit system was also built in an ad-hoc and is at level where full transit lines stop for days at a time. So all that's left is driving, though Boston drivers have a terrible reputation too!
The smallest streets are haphazard. The big stuff was all planned out to make the overall system function well, got 80% done then some special interests kicked money to the right politicians and they stopped progress at 85%. Ditto for the subway. Every couple decades they come up with a grand plan to make it not suck then special interests compromise it out of existence. Boston drivers are fine once you've been there long enough to understand the unwritten rules. If you're naive and think you can follow the letter of the law you will have a bad time.
>Boston's weather is also miserable - the place is at just latitude so that wet, 30 degree weather prevails in winter, giving freezing rain, frozen rain, slush and all manner of nastiness. Plus horrible hot, humid summers. So you have to avoid walking a lot.
The weather is fine. Kids are much more tolerant of weather extremes than their white collar parents (the ones who dominate the debate over this kind of thing) who's days are spent in three different climate controlled boxes (house/apartment, car, office). If you do it every day it's really not a big deal.