useing the fence post is the way to go . using a cement block as a fulcrum and a fence post as a lever to raise up the front of the car and block it up. may take a few times and maybe one side then the other.then get the plywood back under the car as close to the middle as u can. then put the fence post on top of the plywood and let the car down on that and start winching. have the next fence post ready for the front of the car to land on as u winch forward .now u willbe really rolling along and can then start the car up your rampto the trailer. wish i could be there to help.
I had a '41 back in the late 60's. I twas a coupe with a '53 merc bronz block,aluminum wiend heads,wolverine 3/4 cam and of course 3 - 2 barrel prog carb set up with a 411 rear. only problem ,stock tranny .it was still a lot of fun blowing off modern v/8's. Blow off a registry cop one night LOL. but i digress . Have fun with the 41's and post progress.