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Does anybody have any advice on asking for transfer LORs? I ended up doing well in a professor's class, and he seems receptive to the idea of being a reference/writing a LOR for jobs/clerkship purposes.

Employment opportunities don't really factor into this decision (they don't change much by transferring). I want to transfer largely for geography reasons, but "prestige" definitely factors into the equation. With that being said, the professor has been here a while and is an alumni of the school, so I'm afraid that giving off a sense that I'm "transferring up" may be offensive.

I'm going to talk with him early next week. How should I frame my request as to minimize the awkwardness? Am I just overthinking it?

It was awkward as hell for me. My professor asked me about the "prestige" thing. Even worse, he asked what the school could do to keep me. I just said I'm trying to "assess my options" and I wasn't going to make any quick decisions.

PM me if you want. I think what I did worked well.

I told my recommender that I knew I had the grades to transfer, that my career goals would be objectively better suited at a different school. Also that really liked their class and the perspective that they brought to the issues.

Honestly I think you're overthinking it. The professor isn't going to be offended by the thought of you transferring. Just briefly explain your reasoning and they should generally be happy to help, at least IME.