I tried to put cannon ports in her, but they looked awful, so I dropped them. The exercise was to pen up a simple hull, that had high initial stability, yet reasonable sailing lines, low RM and enough seating to place a crew, in effective locations for the string pulling stuff. I don't like the two cockpit arrangement, but I had to have mast purchase somewhere. For hard windward work, you could douse the courses and hang a gollywobbler and staysail between the sticks and she should be fairly effective. At 20' on deck, there's enough internal volume for a reasonable crowd of kids, yet keeps the boat manageable at the ramp, on the trailer and fits in a garage. A FNR 5Hp outboard in a well with wheel steering would make her handy enough. Masts with no taper will be in the 25 pound range if Douglas fir, birdsmouth, less then 20 if spruce. If tapered properly, the spruce sticks could be as low as 14 pounds.
I've changed the upper chine, to make placing gun ports aesthetically pleasing. It affects the entry a little, but not objectionably. I've also taken the drag out of the keel and moved some volume aft, so she'd balance.
That's the boat but I recall at some point he said the lake he is on has an 18ft limit. I'm going by memory which is so so....and there is a solution, move.
He could take it to bigger waters but I think some of the appeal is looking out his window and seeing it at the end of the dock. That's a grin, but so is yelling 'raise the gollywobler!".