You really think Boston is more desirable to most people than Chicago?
I am not from Boston but I would choose it over Chicago because of the ocean is better than a great lake. Fresh sea food beats freshwater fish. Both have cold weather but Boston has more history. We also win NBA history wise. CHI has a better market to make secondary money but the BOS one is bigger geographically with a lot of NE.
That being said CHI didn't bring home a star this year and I doubt BOS will next year. Stars like good weather and good weather places get stars all the time but it did not help LA or Houston this year.
While I agree with your reasoning (plus I'm a sucker for mountains, even East Coast mountains, and as such despise Midwestern geography), I don't know that its nearly as strong a case as you might think. I infinitely prefer Chicago as a city to Boston, which, if we're being honest, is miniscule when it comes to, you know, actually being a city.