While I agree that different ramps can make a difference on which trailer to choose and that a good roller trailer does not require immersion into the water, I don't see the need to have a second person with the float-on. Many times, I have launched and loaded both my old 18 and my current 23 by myself. I used to just hop off the boat and onto the dock, after powering the boat on the trailer. I don't "hop" as well anymore, but I think I could still load the boat without having someone drive the truck out.
As far as dealing with cross winds and current, I would think the roller trailer would be harder without someone pulling on a stern line to keep the boat straight.
When I have someone with me that knows how to back a trailer, I am moving the boat towards the trailer as it gets to the water. It then generally takes less than a minute to have the boat out of the water.
I watched three guys take about 15 minutes getting their boat loaded on a roller trailer that they used as a float-on type. After taking all that time, the boat was crooked on the trailer.
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