Middlebury College Vs UVM Honors

It sounds like you’re fine at UVM.
What you CAN do is maximize your time at UVM, take as many advanced or honors seminars as you can in relevant fields; don’t forget to take art history, music appreciation, and classical or comparative lit courses+ perhaps a foreign language or study abroad in London or Singapore if affordable (if you intend to change social class, it will help - I know it sounds odd but it’s a matter of habitus); use the career center and your advisers to find internships, and externships summer jobs, etc (though it sounds like you’ve been doing that); look into profiles of students admitted to MIT’s relevant MSc and try to meet that.
I actually think UVM may help you more than Middlebury here because you’ll be better at leveraging your advantages rather than having to start from scratch, plus you’ll be able to take more courses (10 vs 8 per year).

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See if you can enroll in 5000 and 6000 level math/CS/stat courses

I suggest courses in probability theory, data science I and II, information theory, complex systems. You could also do an independent study in control theory. You can also build off your MechE background in a computational direction by taking computational solid mechanics, numerical methods for engineer [sic], and multiscale modeling

IMO, combining generalist skills like CS and DS with domain expertise is the best way to have a successful career.

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