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Do these exist? Has anyone extended their clerkship to do this? Pros? Cons?

If you're thinking about trying to extend a two-year clerkship, there might be one logistical problem with that: one big advantage (at least from a district judge's perspective) of having two-year clerks is that they can have staggered terms. Staggered terms are good because there's always one experienced clerk who can help the newly-hired clerk during his first year. If your judge normally hires clerks for two year terms and you ask to extend yours to three, it will fuck up the staggered hiring.

I don't think I've ever seen a 3-year clerk, but that doesn't mean it doesn't happen. However, you can't work as a term clerk for more than 4 years total (not just for the same judge - at all, for any judge), so I think there's a sort of general reluctance to have term clerks keep extending their terms.

(This is in the federal system; I have seen state clerks do this.)