Continue to appreciate the suggestions (most of them).
I bought a pair of multi-purpose scaffolds (aka Perry) from TSC who
had them for $150 each this past weekend. We have only used them
thusfar to get us 2' and 4' above the ground. All I can say is it's
Much better for me than setting up a ladder, climbing, painting a
small section, repeat. I suppose if I was a very good painter, I'd
develop the right muscles and skills to paint rapidly from a ladder,
but for me, the 6' of scaffold space plus another foot to either side
lets me attack 8' of soffit, fascia, siding, etc as if I'm standing on
the ground. One unit alone will get me 6' off the ground which will
be enough to reach 13-14' which is 80% or so of what I need. If I
stack I can get at another 10% or so, leaving that last 10% as the 22'
peaks and a couple of spots on the dormers. Brush on a stick might be
the answer this time -- so long as there's no other prep needed.
Hanging out that bathroom window to get at the dormer on the 12/12 is
an interesting idea. I need to give that some more thought.