My big challenge is going to be painting under boat when it is on the trailer. I will need to find a way to jack it up a bit when I get to that stage.
When I first stripped our boat's bottom, I borrowed a set of car wheel ramps from my buddy. With the trailer wheels on the ramps, the trailer was alot easier to get under.
This year, when I had to antifoul the bottom and keel, I used the ramps again, and then I used a $12 bottle-jack and alot of wood blocks to lift the trailer even higher, then blocked it up safely, removed the trailer wheels, and unbolted the rear of the leaf-springs so the axle swung out of the way and I could lower the keel fully, to clean and antifoul it.
I was planning on putting trailer on blocks to do a lot of hull work. Unfortunately not only do I have boat upgrades to perform but the trailer is in need of a new axle. What I really want to do is build a wooden support for the stern of the boat and then use neighbors backhoe with strap to lift bow so I can pull out trailer then support.
My trailer turned out to be a complete rebuild. Very little of it was salvageable. Tires were split, tongue and cross members corroded thru, wheel bearings and hubs (both sides) failed on the tow home when I bought it, half of one fender still remaining, etc.