I'm not sure on (2), but by jumping on the board, you're doing 2 things, getting air to pass under it, which breaks the drag (friction) caused by the water, hence allowing to 'pop' the board onto the plane...also it reduces your weight for a split second, which in most cases when you're just off planing will allow the board to lift also. Probably not scientific responses, but physics was never my strongest subject...I'm more a "if it works, then that's what you do" guy.

Maybe the pressure on the fin comment means that by putting pressure laterally, you're reducing the downward pressure (weight), and allowing lift??? To achieve this, you'd have to be committed to your harness, or boom, and have the sail leaning back, which is how I find is the best technique for pumping the sail anyways.