Thanks for the feedback!
On the first point, there is a feature which mitigates this a little bit, which is that when you are in travel acceleration, you can rotate instantly by clicking on the compass. When not in travel acceleration, you can do it by control+clicking.
More heeling under bare poles - I'm worried that this would be too much, without the ability to strike the topgallantmasts. For the orientation under bare poles, I don't know. I feel this should depend on how far forward the bare poles are -- I think right now there is no wind drag modelled on the hull, which is maybe also relevant.
Sailing to windward - what do you mean by windward? It's not clear to my why you couldn't in fact sail a ship like a schooner. I suppose the likeliest things are drag from the unused spars, plus staysails not being as efficient (or as big?) as a proper fore-and-aft rig, so these would be the things to model.
I agree the damage stuff is currently not entirely logical. Apparent wind does matter for the sails.