Having the line straight down pole to capstan is good idea, in that forces on pole are inline; but, this would tend to put the ground work(er)s in the kill zone?
Self-tending Prusicks would be good safetys on 4 pulley rig for manual lift. Also, hang on rope and '2 Hand' system, for less effort.
With just 2 pulleys available would consider lowering thru just 1 pulley, with raps around something (pole?) for frictions. To lift, would have 1 pulley at top, 1 low on pole and use slow truck pull (also safest w/ self tending prussick). Pulley at bottom would keep inline force on pole fairly, and only leverage across at low leverage point on pole AND not pull upwards on truck (causing possible traction loss). If clear behind, could also pull with truck backwards, to watch works.