B-School strategy: I have to tell my boss I'm applying to b-school to get his rec this fall. If I don't get in to the one I want, would I have to quit next year? What's the best strategy here?

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Commenting because interested as well.

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Go to your boss with a broader career discussion and not just a request for recommendation. Assuming the boss has gone through a similar experience and is not a moron, it is normal to write recommendations as a boss. If you don't get into your dream school, expanding on your skill set and improving your resume by moving into a different role/company /industry could be a part of your reapplication strategy anyways.

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@MS so the expectation is most likely leave or switch teams if you don't get ur school of choice?

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No. Not an explicit expectation but the schools would like to see that you made an effort to improve your application, as much as possible. You could also stay in the same group in the same or expanded role and improve your test scores and/or find some leadership opportunities outside of work. How well you do at work plays a role in the school's decision as they are trying to assess your probability of future success

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