I have just finished rerigging during my current haulout . As I said I only raise masts occasionally but I figured the counterbalance method was worth a go, plus I was doing this in the privacy of my own driveway and so there was no no looney inventor spectacular at the ramp carpark. I recently added a heavy duty swing up jockey wheel for Spritzig II's trailer and as there is a fair bit of real estate vacant on the draw bar I left the old j.wheel clamp in place . I put an old round steel fence post I had scavenged in the clamp and a pulley hooked over the top rim attached a length of polypropylene rope to the mast and the other tied to a nylex tub to take my counterweight material. The pole was not as high as a would have liked but this was an experiment.
Now my original plan and ultimate plan was to use heavy stuff I already had on the boat ie two anchors and a full fuel tank , however as bad luck would have it the fuel tank was empty and both anchor shackles were frozen shut. So it was back to my original, original plan (see my first post ) water .
After running all my new rigging out and fitting plastic tubes over the shroud turnbuckles as per Jeff's advice someway back and fixing the shrouds and the forestay to the rails and mast with my magic foam fingers ( large foam twist ties I have mentioned before) I was ready for a solo , snag free mast lift.
I filled the nylex cube with water from the hose to full, climbed up and the mast was still fairly weighty . I then added a couple of iron round flat weights and an antique iron scale balance I use as a doorstop in the study. All up I think the total was now about 20 kg, give or take a bit of scrap iron

. I climbed up again and the mast was now much lighter. It was not bouncing like you see in the mast mate videos but was a comfortable lift for me with my stuffed back to the upright position . Even the "leap of faith" from the cockpit seat to the cabin roof was no drama. Only snag was that the cube touched the ground before the mast was fully upright but it was close enough to be past the herniated spinal disc zone. I looped some of the slack around the pulpit and had everything held in place to attach the forestay at my leisure . No fuss , no muss and no rough stuff.
Refinements would be, have a pretied loop in the poly to loop over the Sampson post when the mast is up or I'm sure with a bit of fiddling I could have the post higher so the cube drop would just get to the ground or stay above it when the mast is fully raised. But as an experiment it worked fine.
Now what to do with the pole. Wood would be lighter but I think light gauge steel square section with a round 2" section bolted to the end to fit the jockey clamp would work. This could be carried slid into two brackets on the trailer, but wait there's more.
Wotif you placed brackets on both sides of the trailer then added an L bracket to take an upright? When retrieving in in a cross wind or current, you can extend this square pole out with its upright to give you an extended goal post style guide (with foam covering on the upright) on the down wind side to keep your boat square to the trailer while winching on. One pole, two sets of brackets depending on the wind direction. Or if your touchy about your hull hitting the pole put it on the upwind side with your relocated pulley and pay out a stern line as you winch ( needs two hands ) .
Wotashame I'm moored .....all this trailer/ mast raising stuff is endless fun.
By the way I'm wondering if a modified rig could be used to raise the mast on the water . Two anchors on a rope through a roller mounted on the top of the pushpit. Hmmmmmmm