One of my best friend's Moms had a rowhouse (townhouse for you non Baltimoreans) with an enclosed front porch that had a very leaky roof. In ay storm, large puddles would appear on the floor. Because she was an older woman who lived alone and had little money, hiring a professional to fix the problem was out of the question.
No problem, she had us.
On one of the coolest February days ever (temperature was in the teens) we grabbed a tube of caulk and a caulk gun and headed over there. We had no ladder, but figured we could crawl out on the porch roof from a second story window. It was a little damp as well as cold, but we were manly men and could handle it.
The roof, as it turned out, was slippery slate and had a very steep pitch. Anyone climbing out the window onto the roof would immediately slide off and land on a concrete walk that was a long way down.
My friend, Chip, was (and is) deathly afraid of heights, so the person on the roof was going to be me. Luckily, Chip was also larger and stronger than me, and together we hatched our plan: He would tie a rope around my waist and lower me out the window, so I could hang over the edge of the roof and caulk the eaves (where we were sure the leak was). To ease his load, since we had no pulley, we decided that Chip would loop the rope around a cast iron radiator that was near the window.
With the wind blowing, adding wind chill to the ass freezing cold temperature, I crawled out the window head first and crawled/slid to the edge of the roof. I began frantically caulking every gap in sight while hanging upside down, my head 20 feet above the concrete walkway, hoping to use up the tube of caulk before it or my fingers froze. (Oh, yes, we'd neglected to bring gloves.)
I scrabbled along the edge of the roof upside down, caulking like a maniac, until the tube was empty.
It was noisy on the street, and the blowing wind didn't help. "Chip, I'm done. Haul me in." "What?" "Pull me in." "What?!" "PULL ME IN!"
Inch by inch, with a few fits and starts (a cast iron radiator makes a lousy pulley), Chip pulled me back in. Half frozen and dizzy from hanging upside down, as well as a little damp from the roof, I was relieved to be inside. Chip's Mom made us hot chocolate (we were in our late 20s at the time), and we strutted around the house like Testosterone On Parade.
It rained the next day. The roof leaked like a sieve.
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