If one of the motivators for Boston is proximity to top tier universities, as a data point of one I had zero desire to stay in Boston after school and didn't think to get a job in the area. I doubt I would have stayed for Amazon.
And the winter.
I went back last year in October. 20 years is a long time, but the traffic now reminds me of Manhattan (apparently the bad drivers are called Mass-holes), with screaming cabbies and bumper cars.
I did have the best clam chowder of my entire life there, so there is that.