I owned a Pearson 27 (draft 3''4") with a winged keel for 15 years, and last fall bought a Pearson 33 (draft 4''2") with a winged keel. Obviously I like the wing or I wouldn''t have bought the 33.
My experience has been that with the shoal draft, you''re a lot less likely to run aground to begin with. But if you do, yes, you have a lot more surface area contacting the bottom than with a fin. Best way to get off is to power off with the boat as flat as possible. Heel it any and the wing digs deeper.
I''ve only touched bottom twice and both times the keel bounced off the bottom (mud both times) and the boat kept going. I probably was lucky, but the keel didn''t dig in. I think a fin would have in those two cases.
As for crab pots here on the Chesapeake, have never grabbed one with the wing. I had the anchor rode wrap around the keel exactly once in all those years -- and all I had to do was let out more rode. It dropped off the keel and the problem fixed itself.
As for the bottom of the wing being shaped like a plow anchor -- no way for the Pearson wing design. The bottom of the Pearson keel is shaped more like a Bruce anchor.
In other words, pay attention to your depth meter because you don''t want to go hard aground, and you''ll be fine.
Email me directly if you have more questions.