This is another question rather than a reply. My boat is a 22' Oday shoal draft (23"). My problem is leeway when pointing as high as possible. It seems that I have to bear off a little more than my competitors to maintain speed therefore a better VMG. To check between my compass and my gps I'll motor downwind where leeway won't be a factor. My compass on the bulkhead and heading on the gps is very close. When I'm sailing upwind sometime I get as much as 8 degrees difference. I'm not sure if it's a matter of just design or my sailing skill and sail trim. Ready to learn.
Oldironnut, I have raced against Odays in that size range, and they point about as well as most other cruiser/racers in that size range. A boat with shoal draft will usually lose a very little pointing ability. But, what really reduces your boat's pointing ability is poor sail trim, poor helmsmanship, and anything that reduces your boat's speed. If the underwater surfaces are fouled by dirt, or slime, or many layers of old, peeling paint, that roughness creates drag, and disrupts the smooth, laminar flow of water over the hull and keel, and it creates turbulence. Serious racers at least scrub the bottom before a race, and are meticulous about preparing the bottom each spring.
No matter how much skill the skipper has, a sailboat can't be competitive if it has a foul bottom and can't generate speeds that are comparable to it's competitors, so your first priority should probably be to make the bottom smooth and fast. Then, work on sail trim, boat handling and helmsmanship, and practice, practice, practice. Also, volunteer to crew for other, experienced racers, and watch how they trim their sails and handle the boat, and you'll learn fast.