So, it took several months but I finally got to take the new (to me) kayak and trailer out today for the first time. It took several weeks to strip the trailer down and re-build it, combined with several months of patience waiting for the right kayak deal to come along.
I am still fine tuning the kayak saddles. They are kind of persnickety. The J-hook rack is for a 10 footer for the boy as soon as my finances recover. I should have bought shares in Elliot's Hardware before I started this rebuild. The good news, I am officially a kayaker now.