I swear, roofs are like the ultimate “out of sight, out of mind” headache. I used to only check valleys and flashing when someone complained or when there was an obvious issue, but after getting burned by a sneaky leak (literally dripped right onto my laptop... not cool), I started doing a quick walkaround every few months. Still, even with regular checks, it’s easy to miss stuff—especially if you’ve got a steep pitch or a ton of weird angles.
Honestly, sometimes it does feel like luck plays a part. I’ve seen two buildings on the same block: one gets shredded in a storm, the other just shrugs it off. But usually when you dig into it, there’s something small—a nail popped up, flashing bent just enough—that explains why one failed and the other didn’t.
I try to focus on the details now. If I can’t remember the last time someone looked at the flashing or checked for loose shingles, that’s my cue. But yeah, you could spend your whole life up there and still miss something tiny. Nature always finds that one weak spot...
Totally get where you’re coming from. I used to think I was on top of things just by eyeballing the roof from the ground, but after a windstorm last year, I found a shingle halfway down the yard and realized I’d missed a bunch of stuff up there. My place has a low slope, so it’s not even that hard to check, but there’s always something hiding—especially around those vent pipes and the back side where moss likes to sneak in.
I do think luck plays a part, but like you said, it’s usually the little stuff that adds up. My neighbor’s roof looked fine until a storm peeled back a corner, and when we checked, the nails were barely biting into the decking. Meanwhile, my old three-tab shingles somehow held on, probably just because I’d re-nailed a few loose ones the year before.
Honestly, I wish I’d started taking photos during my checks—would’ve made it easier to spot changes over time. Still, even with all that, sometimes it feels like you’re just rolling the dice with Mother Nature.
Never fails—every time I think I’ve got a roof handled, something sneaks up. I manage a few older duplexes, and after that last big storm, I did a walkaround thinking it all looked fine. Then I crawled up there and found a whole section of flashing that had peeled back behind a chimney, just out of sight from the ground. No leaks yet, but it was close.
I get what you mean about luck versus maintenance. Sometimes it feels like you can do everything right and still get hit with a surprise. But I’ve noticed the places where we keep up with the little stuff—like clearing moss, checking under vent boots, making sure gutters are draining—tend to hold up better in storms. Not perfect, but fewer emergencies.
I’m with you on photos. Started snapping pics during inspections last year, and it’s already helped catch a couple of changes before they turned into problems. Still, even with all the prep, sometimes it just comes down to whether the wind decides to hit you or the neighbor harder.
Honestly, I’d push back a little on the “luck” side of things. Sure, a direct hit from a tornado is just bad fortune, but most of the issues I’ve seen over the years come down to details that get missed during regular upkeep.
- Flashing is a big one—like you said, it’s almost always out of sight. I make it a habit to check every joint and seam twice a year, not just after storms.
- Photos are great, but I’d argue hands-on checks matter more. I’ve spotted soft decking and loose nails by feel that never showed up in a picture.
- Gutters and moss are important, but old caulking around vents and chimneys is what’s bitten me before. That stuff cracks way faster than you’d think, especially with freeze/thaw cycles.
I get that some storms are just too much, but in my experience, 90% of “surprises” were actually slow burns I could’ve caught earlier if I’d looked closer... or just crawled up there more often. Maybe it’s not luck so much as how obsessive you’re willing to be about the boring stuff.
Luck’s overrated—maintenance is everything. I’ve seen “lucky” roofs fail after a mild storm just because nobody bothered to check the flashing or sealant for years. It’s the little stuff, always. If you’re not crawling around up there, you’re gambling, plain and simple.
