Back to sailing fundamentals: 1. Especially on a Sunfish, don't sheet in too much going upwind. On starboard tack one can sheet in a bit more; having the clew above the corner of the stern is about right.
2. Learn to roll tack 3. Use a vane on the upper spar (gaff). Can be as simple as a clothes hanger with tape (remember tape?). With your favorite music of course.
2) There's space under the deck—at the bridle—for a motorcycle battery strapped-in on one side, and a trolling motor bracket on the other. The two boxes can be made self-bailing. The trolling motor shaft can be cut shorter, and all the [labeled] wires slipped off the hand control/tiller. (To be reconnected later to the control/tiller). Wires can be fed under the bridle area. The connexions can be simplified, as you don't need reverse or variable speeds..
The prevailing wind blows directly on to our beach so an easy tack port or starboard gets me well of the beach then i can reach all day and run home. With a combination of uphaul and gooseneck locations I keep the boom high at the cockpit to allow my old stiff bones to duck under for a good clean tack