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I'm a 3L at SLS and have a district court clerkship for 2019 (after returning to my summer firm for a year) in a popular district (think NDCA, SDNY, EDNY, DDC) and am thinking about applying for appellate clerkships for 2020 in the corresponding circuits (thus 9th, 2nd, DC). How much does a prior district court clerkship help, and is there anything specific to do to leverage that into an appellate clerkship without having started it?

My judge, who is in one of those circuits, has a heavy preference for former clerks, so I'd certainly include it on the cover letter and resume to get at least my chambers to do more than a cursory look. But the judge maintains high standards for grades/other credentials/etc. and does not lower them in light of the former clerkship, even one from a competitive district.

Yeah, I think the best you can do is probably putting it on your resume as an anticipated position and highlighting it in your cover letter. It definitely can help enough that you should include it.