For your possibility 2 one just use Jacoby and jump in the water and throw bombs at them. Once you've done that you can just use the gold crank to lift the bridge and there goes the red hat.
EDIT: This is extra hearts, which you already have. Use Jacoby instead of trying to shoot from above water.
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Last edited by Cinderkin; 05-08-2011 at 10:50 PM.