ASA and PSIA Instructor
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This depends on whether his shrouds are inboard or outboard. But even then, somebody asking this question probably does not have a huge demand for super-high pointing ability, and if he goes inside the shrouds and doesn't have an alternate sail for broad reaches, he could have chafe problems.
The question of inboard versus outboard shrouds only affects how close you can trim, if trimming inboard or if trimming outboard, but I can't see how it affects the decision as to to trimming inside or outside.
Trimming a jib outside which could be trimmed inside, probably adds about 15-20 degrees to the tacking angle, a material hit to performance which one is of course free to choose to accept. As to the chafing, unless you are on a point of sail for a few days it is not a material consideration.
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