Just wanted to share this as maybe others might be interested.
I found a carpentry board roller made to use with a table saw at Sears. It is designed to support the end of a board while cutting. It has a very sturdy roller and was bolted to a stand.
I removed the stand by unbolting the one screw and then drilled out the bracket and mounted it on the end of my raft trailer rail. I think this will make loading much easier and it only cost about $50 and a half hour.
Here is a link to the roller stand from sears:
Sears: Online department store featuring appliances, tools, fitness equipment and more
Here is an after the instal pic on my trailer: