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See below, straight from Boston Whaler. One thing I was not aware of is that all-roller trailers should not be used with Whalers. Personally, I wouldn't use one on any boat.

Depending on the size of your boat and the conditions in which you launch and retrieve, there are two styles of trailers:


1) Float-on bunk style trailer - Bunks should be as long as possible and conform to the shape of the hull to provide good fore and aft support to spread the total weight. For larger/heavier models, you may want to look into two sets of bunks. One set to cradle the keel and another further out for support. Keel rollers or guards can be used on the trailer cross members to provide additional support or protection. A float-on trailer is easier to maintain and works best in boat ramps with deeper water.


2) Keel roller trailer - Keel rollers must be adjusted so that they support the keel and bear ALL THE WEIGHT of the boat. Side bunks should be used to balance the weight on the keel rollers. A keel roller trailer works best in shallow water ramps.


Boston Whaler does NOT recommend using an all roller trailer. Side rollers can cause a ripple effect on the fiberglass. This can disrupt the bond between the fiberglass and the foam core, causing potential hull problems.