Well... some things work and some don't.
After two raisings, I have come to a determination: The method of raising the Reaper (illustrated below) works fine on paper, but does not work well in real life.
The biggest problem is that I can't get the pulley high enough to gain decent mechanical advantage when it's needed most. The result is that I need to raise the torso using direct muscle power. This is not good engineering.
There are quite a few ways to resolve this problem, I could rent a scissor-lift every year, I could build a crane on my roof, I could just leave the Reaper up all year round, ...or I could just eliminate the need to raise the torso.
The plan now is to simply weld the torso to the base, add some embellishments, and do strange and unusual things with it all year round.
Wish me luck.