Thanks Rolf
Generally the wind is a cross wind or a quartering tailwind so everything conspires against it. You are right about the optimum way being to raise it into wind though.

After I wrote the post I realized that maybe my solution is to use what everyone around here calls a "pull-off", which is a setup where an anchor is installed a short distance off the beach. Then a rope comes from that (rope length is 3 times the depth of the water) to a wooden cross with a hole drilled into each end of one of the pieces of wood. Also a bolt is put through the wood, outboard of the holes, perpendicular to the holes to keep the wood from splitting and releasing the ropes. The other hole is then enlarged and smoothed out with a router and a rope goes from there to the beach around a permanent post of some sort and back out to the cross and is attached to the rope forming a loop.

Then a buoy (Plastic bottle) is attached to the rope with a length of rope is attached to that to fasten to the boat.
Then you attach the boat and use the rope to ...... jokes off... pull the boat out to the cross where you are moored and can raise the sail into wind. I have discovered that it is best to moor the boat from the most forward part of the boat in the centre (spinnaker snuffer on my Tiger) with a length of rope to pull the slip knot to release the boat as it is hard to climb out front when singlehanding as I generally am.

Regarding the sail I was referring to the direction of rolling the sail. When I got the sail I seem to recall that it was rolled in such a way that when it was coming off of the mast it had to bend outward and then back inward to go onto the roll. Now I have reversed it so it rolls in one continuous direction as it comes out of the mast.

That was interesting about rolling from the top first but I suspect that when you factor in the part about having to unroll the whole sail and have it flop around on the ground, you have effectively negated any advantage that you got from rolling it up the other way.