I'll take a stab. Try not backing down so far in the water. Most errors on the boatramp I see are from people backing the trailer so far down in the water there is little there to guide anything but the bow onto the trailer. I have a bow pulpit on a Boston Whaler that has given me fits on and off the trailer. It keeps wanting to catch on the winch stand. The prior owner nearly ripped it off. I have found that if I leave more of the trailer out of the water the keel will find the front v-guide (roller) and raise the bow to the point where the pulpit clears the winch stand. With properly functioning rollers you shouldn't need to bury the trailer. It might be worth a try. Another note, the keel roller in your picture is very narrow. If you are driving it on the trailer a little more width might make it easier, if something could be adapted there.
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