RKC,
I am not sure where you are located, here is what I did with mine during my restoration, I found a handy man on Criaig's and paid him to do the sanding and prep work it in my driveway cost me 100 dollars (agreed up front)
I now found a mobile media blasting service here in Orlando (bummer) after the fact!
I however prep the Boat by placing it on blocks ( which I return to the store) once I was done with it not all since I painted a few :)
Unhook the Boat from the vehicle and lower the jack on the trailer all the down this will raise the transom up. Insert the blocks and then jack her up this will semi clear the back of the trailer, now link the trailer on the truck and secure it, slowly ease forward whilst a person stands by the trailer winch to quickly lock if the hull attempts be pulled off the blocks, I inserted blocks in the middle supporting as I go along, note 2 plus man job here.
If you have a stationary something at the back of the hull attach her to it, it will prevent the hull from moving forward with the trailer and off the blocks.
In my case the House was not an option :)
Use 3/4 ply on top of the blocks never have the hull in contact with the cement blocks.
I use a automotive 3 ton jack in the middle to roll her side to side moving the blocks around the paint job to complete the Gel Coat process.
During the painting process only use carpet on top of the ply to prevent paint peeling off (do not use carpet during the trailer removal process) it will work against you.
Inserting the trailer is a breeze
Soap up the trailer rollers, bunks and all, wet the entire bottom of the boat use (Laundry detergent) and please keep her linked on to the truck and slowly back the trailer under it, hook up the winch and once half way there crank her right on. Mine slide right on to the complete amazement to my friends and spectators!
Please be careful and err on the side of caution like I did use extra blocks, do NOT use there blocks on its sides always use in the upright position for maximum strength.

See this rim under the Boat? It was not use, however when I was under the Boat guess what was next me?
I arrange the Bocks for max support

Here I moved the blocks forward for painting

Here is a picture of the jack