Case 14: In the photo below, W9235 is outpointing W3854 as they sail up a beat on Tawas Bay.
1. If they continue to get closer together to the point of nearly colliding, who will have to keep clear? Under what rule?
2. Would rule 17 apply here (same tack; proper course)?

3. What other rule will apply once these boats get very close to each other, say about a foot of water between the hulls?

1. It will be a straightforward case of rule 11 (windward/leeward), and W3854 (Uncle Al) will have to keep clear of Brian Jeffs (9235).
2. Rule 17 is not likely to apply since it is extremely rare that a boat is able to establish an overlap from clear astern and within two boatlengths while going upwind. Even if this did happen, and I've been on some lakes (Clark Lake, Lake Orion, Fanshawe) where it does, Leeward would be entitled to sail (no higher than) her proper course which could include any amount of "pinching" she cares to do.
For what it's worth, if 3854 (the windward boat) wants to sail down onto a boat trying to pass to leeward, he may do so. Of course, rule 11 still applies, and 3854 will have to keep clear of 9235.
3. Once the boats get into close proximity, rule 16.1 kicks in, and the leeward boat must take care not to change course - for any reason - if such a course change does not leave Windward room to keep clear. On the other hand, Leeward is entitled to hold his course, and if Windward can't point high enough to keep clear, he will have to tack away or luff up and let Leeward go by. If  Al leaves tacking or luffing up too late and can't do so without colliding, he has not kept clear - see definition of keeping clear - and must do his turns.

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