At the risk of sounding like a Cassandra, is these the lines of the boat we're talking about?
O'DAY 272 sailboat specifications and details on sailboatdata.com
If so, do you have enough keel here to avoid sideslip? You draw under 3 feet, which seems kinda short-legged to me. Heel her, and much of that is shadowed behind turn of the leeward bilge.
I would have expected another foot of keel here, wings or not or, absent wings, then a centerboard that drops down for upwind work. It hurts me to say this about a Ray Hunt (office) design, since I grew up in 110s.
I would like to be wrong about this, and I've never sailed one. But that's what it looks like to me