Windward ability is a fetish carried over from the
racing nuts. In real life, windward ability is very very seldom an issue on a cruising
boat. Going to
weather may be fun and a challenge for a daysail but gets really really old when you are doing it 24/7. It gets especially painful when there is any kind of a sea running which there almost always is away from land. Almost everyone plans a
cruise to have the winds at a close reach at worst. Doesn't always
work out but the few degree difference between a
boat optimized for windward
work and a typical cruiser just isn't that great. It's especially not that great when you take crew fatigue into the equation.
For coastal cruising windward ability has a bit more relevance but it depends on where you sail. If you have long slogs hard on the prevailing
wind to get to your favorite anchorage or cruising
destination, a few degrees of pointing ability can make you feel better about not having to tack to lay it. Then again, turning on the
engine and running it at low
rpm motor sailing will let you outpoint even the closest winded boat and burn very littel
fuel doing it.
A
shallow draft wing keeled boat won't point as high as a deep keel boat. But for all practical purposes in the real world, it ain't no big thing. You may never have occasion to take advantage of the few degress higher pointing ability of a deep keel. You may regret a lot more having the extra
draft of deep keel boat if you sail in thin
water.