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Proper Course: A course a boat would sail to finish as soon as possible in the absence
of the other boats referred to in the rule using the term. A boat has no proper course
before her starting signal.
That''s the RRS definition, but that shouldn''t be taken to mean that there is a proscription on a boat to sail that course. There are a few rules that use the definition, but generally, there isn''t a rule that says a boat must sail a proper course.
In your specific case, if a boat establishes an ovelap to leeward from behind, she can''t then luff the windward boat. But if a boat overtakes to windward, the leeward boat can luff her without limit, provided she gives the windward boat ''room'' to ''keep clear'' (which are two more defined terms in the rulebook).
As your note implies, there are more cases when proper course becomes relevant at mark roundings, as when otherwise burdened boats establish inside overlaps, and can not then use their rights to room at the mark to prevent outside boats from also rounding reasonably.
Crystal clear, right?