The Seaward is said to have a robust hull structure, but indeed the videos I linked above do show an extreme approach and considerable stress on the hull. I would be thinking of a trailer sitting a foot deeper, maybe two feet. With my O'Day on bunks I have my truck rear wheels touching the water and the trailer fully immersed. This makes recovery easy but often a little wet for yours truly. Well, always a little wet. The O'Day has a flat bottom and so rollers would be an easy modification. The problem with the Seaward is the shallow, short, fixed keel with fins at the rear. Tipping rollers would have to be, as you suggest, high enough to clear this. Expensive parts, but available, and since the boat ramp is the most stressful part of sailing, for me at least, the expense would be worthwhile for a system that worked simply and well.