I'm pretty comfortable at any height 14' and under. I have no problem on the little ladders. It's when the ladder goes thirty feet that I get all twitchy and nervous.
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The peak of the garage is about 25'. Even with the ladder extended all the way up into that triangle over the arched window, painting that trim requires leaning backward away from the siding to reach over your head. I did the garage first so that I could get used to the terror. The peak at the back of the house is about six feet higher, with less options for placing the ladder. That was quite scary.
See? Scary. (But I managed to get a shot or two, so it must not have been that bad...)
My initial estimates had the job of painting all of the trim on the house at about sixteen hours of labor. Actual time ended up being 37 hours of labor. At least everything is now a crisp, bright white instead of the yellowish off-white that is was before. Next step: convince Cari to let me change the doors from red to gray.