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Yes, the commute is crazy by car. Very crazy.
Not sure why you mention the South End as a possible residence. It's neither affordable now a likely place for a child or public schools. I think people who afford the South End (not in public housing) send their kids to private school.
From Malden, you can take the Orange Line into downtown and transfer to a Green Line for Longwood. Not sure what the public transport is for West Roxbury (bus?).
If you could squeeze yourself into living in Brookline, you'd have great access to the possible work sites, wonderful schools, and a very urbane and civilized daily life. If I had a kid, I'd try my hardest to find a way to live in Brookline.
Best wishes.
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