That’s a solid point about the valleys—those spots always seem to go first. I’ve been surprised more than once by what’s lurking under old decking, especially around chimneys and low spots. Sometimes you just have to do what you can with the time and weather you’ve got... not every job gets the perfect prep, and that’s just reality. Hang in there—sounds like you’re handling it as well as anyone could.
Yeah, valleys and those low-lying spots are always trouble. I’ve found flashing around chimneys can hide a lot of rot too—sometimes you don’t know how bad it is till you pull things apart. Weather windows are never long enough, either... just gotta do your best and keep moving.
Yeah, I hear you on the flashing. When we first moved in, I figured the leaks were just from old shingles, but the real mess was hiding under the metal around the skylight. Felt like a never-ending project once we started pulling stuff off. Honestly, I’m still not convinced we found everything, but at some point you just have to stop chasing every little thing or you’ll go nuts. Weather definitely doesn’t help—seems like it rains every time I try to get anything done.
Honestly, I’m still not convinced we found everything, but at some point you just have to stop chasing every little thing or you’ll go nuts.
That right there sums up almost every older roof I've dealt with. You start out thinking it's just a shingle job, then before you know it, you're knee-deep in mystery leaks and wondering if the house is secretly trying to keep you humble. Skylights are notorious for this—I've lost count of how many times I've seen water sneak in around the flashing, especially on roofs that have seen a few decades.
The weather really does seem to have a sixth sense for when you're planning to work, doesn't it? I've had entire crews standing around watching the radar, waiting for a break in the clouds. Honestly, sometimes I think the only thing more unpredictable than an old roof is spring weather.
If it helps at all, I've found that once you get the flashing right—especially around things like skylights and chimneys—you've solved about 80% of your problems. The tough part is knowing when to call it "good enough." Perfection’s a nice idea, but with older homes, sometimes you just have to accept a little character (or “charm,” as realtors like to call it).
One thing I’d suggest: if you haven’t already, check inside the attic after a good rain. Sometimes leaks show up there before they’re visible elsewhere. And if you ever get tired of chasing drips, there’s no shame in bringing in a pro for an extra set of eyes. Even after all these years, I still do that from time to time.
Hang in there—the satisfaction when it finally stays dry is worth all the hassle... or at least that’s what I tell myself every time I see another dark cloud rolling in.
I totally get what you mean about “charm”—sometimes it feels like a polite way of saying “perpetual maintenance required.” I’ve had a few older homes where the roof was basically a full-time hobby. Curious, have you ever considered upgrading to something like standing seam metal or even slate? I know it’s a bigger investment, but honestly, the peace of mind (and the look) can be worth it, especially if you’re tired of chasing leaks every season. Just wondering if anyone’s made that leap and how it worked out for them...