Jon
The sentence "Chuck lays one on Jon, a beauty!" is not a sailing term I am familiar with. I suspect that if some guy named Chuck "laid one on me", I would ask my parents if Chuck was adopted.
Having said that, here is my opinion:
The situation you have described is a common one.
Rules that apply:
At position 1, Jon is the Yellow starboard tack ROW boat. Chuck is the Blue port tack Keep Clear boat.
Rule 10: Chuck must Keep Clear of Jon.
At Position 2: Chuck tacks onto starboard to leeward of Jon
Rule 13: Chuck must keep clear of Jon while tacking.
At Position 3: Chuck has completed his tack onto starboard
Rule 11: After Chuck tacks onto Starboard, leeward of John, Chuck is now the ROW boat and Jon must immediately start to Keep Clear of Chuck.
Rule 15: Requires Chuck to provide room and opportunity for Jon to initially keep clear.
At position 4: Chuck is now luffing Jon but does not luff above "Head to Wind"
Rule 16: As Chuck changes his compass course to windward, he must continue to provide room and opportunity for Jon to Keep Clear. Once he passes Head to Wind, he is tacking (Rule 13) and would be required to keep clear of Jon.
You mention that Rule 17.1 requires Chuck to not sail above his proper course.
Rule 17 use to have 2 parts but now has only has 1 part. Rule 17 only applies when the overlap began from
clear astern within 2 boat lengths. Since Chuck did not obtain the overlap from clear astern, but as a result of tacking (Lee Bowed), Rule 17 does not apply to Chuck and he has full luffing rights and can luff up to head to wind. If you are forced to tack to keep clear of Chuck, that is what you must do.
17 ON THE SAME TACK; PROPER COURSE
If a boat clear astern becomes overlapped within two of her hull lengths to leeward of a boat on the same tack, she shall not sail above her proper course while they remain on the same tack and overlapped within that distance, unless in doing so she promptly sails astern of the other boat. This rule does not apply if the overlap begins while the windward boat is required by rule 13 to keep clear.As always, Rule 14 applies to both boats.