The portion of the chimney that sticks out above my roof is covered on
all four sides with wood siding - which needs repainting. What's the
best way for a homeowner to accomplish this task? I want to use a
roller so I need some kind of contraption to keep the roller pan level
on the roof. It's a one-story house and the roof line is just a little
over 8 ft above ground.

Thanks for any advice.