Maybe the thing to do is to get a ride on some other boats so you have a better idea of what to expect. "More windage" is a relative term, and its effect will vary a lot depending upon how deep and long your keel or centerboard are, as well as how tall or short the
rig is. How hard the wind blows makes a difference too. Around here, 25 knots of breeze may make people re-think heading out, while it''s the norm in other places.