Holy crack! man you're right, be glad the insc co is on that claim or that boat is DOA. It looks to me like the front riser is WAY too low. There should be a constant curve in the bunk from frt to rear but since the frt riser is too low the cntr one is supporting the boat amidship in its very weakest place.
Your trailer guy simply needs to slightly raise the entire boat off the trailer until the CB is a few inches free from the boat(w/ boat parallel to the frame). I'd install new bunk boards and carpet in case the boards retain a memory. Then pull/jack each riser to equal heights in relation to the hull. That bow roller should then be set to take about 30-50lbs of load which he can adjust by using a small hydraulic jack to raise the bow to set the roller height.
Go all the way through the brakes/bearings/lights while you're at it and you'll save yourself an eventual trailer sailor disappointment. Gotta pour love and tlc on that trailer or it'll punish your boat and totally screw up your past time.
Hope the note makes sense. Happy sailing.
M&K
(continuous curve, cushy carpet, solid design, multiple points of support in strongest locations on boat, no pressure on CB, CB guides help retrieval very much)