My poor roofers — our house is apparently VERY difficult. (Two of the roofers we tried to get estimates from just turned us down flat, because they said it was too hard a project!) They did the front half, and then decided to take a break and do the garage before tackling the back half.
I asked them if I could go up and take a look at the particularly bad spot, what they were calling THE PIT, where we’re getting all the leaking. They didn’t quite believe I was serious at first, I think, but then they laughed and said sure.
That was definitely a bit of a project! First step was easy — ladder to the top of the porch roof. I actually walk around there every year to hang the Christmas lights, though I usually just go out the library window for access.
Second step — if you look to the right, where the redbud tree is, picture the porch roof coming out there (around the midpoint of the third picture). They nailed a few boards into the porch roof, and used those to brace a ladder up to the third story. That was also easy to climb, though it took a little wriggling and hanging onto a sturdy rope for stability when I got to the top of the ladder, in order to get my feet onto the boards they’d nailed to that third story piece of roof.
The last piece was a bit challenging — essentially walking up the 45 degree angle, holding onto the rope, to get to the peak. They told me to wear good hiking boots, which I did, so I didn’t have any difficulty with traction, but still, I’m not really used to that kind of thing.
And I was being VERY cautious, so I didn’t try to go upright at all; I basically shimmied my way up, lying close to flat to the roofline. Which was fine, except I should’ve worn pants instead of shorts, as I scraped up my legs a little bit. And even my jean shorts managed to snag something and tear a bit — oops. Oh well.
When I was mostly up, one of the guys sitting on the roof peak reached down and grabbed my hand, helping me up the last bit — he had a VERY firm grip. Very helpful! So I just kept holding onto him while I looked over the peak into THE PIT.
Once I was there, it was clear what the problem was. We added that tower, you know — I really wanted a turret for my home office, and it felt like our Victorian house was sad, not to have a turret. You can’t see it so clearly because of the tree branch in front of it, sorry. But the problem is that one side of the tower goes straight up, but then the eaves of the tower roof cover most of the gap between that and the peak of the main house roof. So rain can fall in there no problem, but it’s very shaded, so in winter, ice dams form and water collects there and over time, the wood rots, and then you get leaking.
It took about ten years for the water to work its way through the shingles and waterproofing and wood, and I need to talk to the roofer about whether there’s anything they can do to avoid the problem in the future. You can lay low-voltage lines for melting ice dams, but he pointed out that you have to remember to be very careful about turning those off, or you can burn your house down, and I’m not sure I trust me and Kevin to be that responsible.
I want to ask him Monday whether he could lay down a V of copper flashing or something on a bit of an angle, to try to reduce the chance of water sitting there. But I’m honestly not sure that’ll work — I think it’s more that in winter, little bits of snow and water freeze in layers, and don’t melt, and slowly wear it out. But maybe he can reinforce the area a bit more. This probably isn’t anything we’re going to have to deal with in the next decade, but I hate to leave a known problem for the next owners.
Well, anyway, that was my little roof adventure. Fun! And the guys were clearly impressed that I wasn’t scared, which is always nice. 
I’m not afraid of heights, though I did wish I had a little more arm and leg strength for that last haul up the rope — clearly, need to do more working out with my trainer and build up those muscles!
