I use a similar gin pole as you. But instead of the block & tackle, I put a block foreword and run the line back to my main winch. My wife does the cranking while I keep the mast centered. That way she can cleat off if needed. With your added mast weight, I can see where my single speed winch would be hard to crank.
I don't see the A frame set up. I've heard of this done by modifying the shrouds somehow to keep the mast centered so there is no danger of loosing the mast sideways. Is this what you are doing?
Here are some pictures of my mast rest set up.
And a quick sketch of gin pole.
Rehoboth Bay/Indian River, DE
S/Y KJ, Helms 25