Welcome to the forum.
Because you have a DS1, I normally would have moved your thread to the "DS1" section of the forum, but since you are asking a trailer question, I'm moving it to "Miscellaneous".
We've had a number of discussions of just that question. You should easily be able to scroll back a bit and find different opinions.
This is my trailer setup. Next time I do the bunks they'll be widened, compared to what you see there. My personal setup is that the rearmost roller sits pretty low and has a V and a groove. It's meant to catch and "trap" the bow of the boat, so I put it at waterline when retrieving. The next roller sits a bit higher so the boat gets lifted out of the water. The bunks are set so that they take over the weight. As the bow rolls onto the forward rollers the hull slides on the bunks. The net effect is that the boat loads straight every time, as long as the bow makes it onto the first roller.
I am usually able to manually pull the boat about to the halfway point, after that, I need help from the trailer winch. If I need to retrieve from a location with lots of waves and / or crosswind, I tie a guide rope to the upwind stern cleat and have a crew member prevent the stern from blowing downwind.
I've set the rollers so they carry weight all the way to about the CB area, but anything aft of that rests on the bunks. (I have a DS1, so the bunks sit close to the place where the seats rise from the hull. That acts to reinforce the hull at that location. One roller is positioned so it holds the CB up. That way the CB does not need to hang from the handle during transport.
That's my take on things, and, as I mentioned, you may find other input in the archived discussions.