Should I transfer from HYP to Stanford?

Right. You forgot another con:

Dealing with not getting in (by far the most likely scenario) and all that sacrifice for naught.

Your thought process seems rather silly, TBH, and, well, the way I would expect a non-adult to think.
For one, you are not stuck in the Northeast forever. You’ll have plenty of decades to enjoy the weather and bike if you care to move after graduation.

For another, the entrepreneurial environment at Stanford would be available to you if you get in to grad school there.
For a third, Princeton, at least, has a finance center and Harvard is plenty entrepreneurial.

BTW, have you heard of the smoke and wildfires that visit CA every year these days?