I would recommend it, because unless you are sure your boat is made from vinylester or similar, it will eventually weaken that area. Polyester is porous on a microscopic level.
question 2:
It depends entirely on the sea conditions and the technique you are using. If you are using the rudder to lift the boat over wave crests and drive into troughs in a medium chop, then you need some heel.
If you were in almost flat wave conditions, perhaps close to shore in an offshore wind and with a similar strength wind, you'd be quite flat.
Trim is a personal trial and error exercise that depends on your style and body weight.
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