"Turned out water was getting in through some loose flashing around the chimney, not even the shingles themselves."
Yeah, flashing issues can be sneaky like that. Had a similar thing happen at my old place—spent ages checking shingles and gutters, convinced it had to be something obvious. Turned out the leak was from a tiny gap around a vent pipe. Took forever to pinpoint, but once fixed, no more mystery stains on the ceiling.
Roof problems always seem daunting at first, but you're already on the right track by paying attention early. Definitely better to tackle it now before it snowballs into something bigger (and pricier). Plus, it's a good chance to consider upgrades—maybe even look into green roofing options if you're feeling adventurous. Either way, you've got this.
Flashing around chimneys and vents can definitely be tricky, but honestly, have you checked your attic ventilation lately? I spent weeks chasing down a leak that turned out to be condensation buildup from poor airflow up there. Thought it was flashing or shingles too, but nope—just needed better vents. Might be worth a quick look before diving into bigger upgrades or repairs...
Had a similar thing happen when I first moved in—spent days convinced my roof was shot. Turned out the attic was basically a sauna from poor airflow. You're probably onto something with ventilation, saved me a ton of hassle and cash...
Good catch on the ventilation issue—it's surprising how often attic airflow gets overlooked. I've seen plenty of roofs replaced prematurely because homeowners jumped straight to leaks or damage without checking ventilation first. Proper airflow can extend your roof's lifespan significantly and save you from unnecessary expenses down the road. Glad you figured it out early... sounds like you dodged a bullet there.
You're spot on about ventilation being overlooked. Had a similar issue myself a couple years back—noticed some weird moisture buildup and figured it was a leak, but after poking around, turned out my attic vents were totally blocked by insulation. Easy fix once I knew what I was dealing with: just had to clear away the insulation around the soffit vents, added some vent baffles to keep things flowing properly, and installed a ridge vent for good measure. Roof's been dry as a bone ever since.
One thing I'd add is that even if your ventilation seems okay now, it's worth checking again seasonally. Changes in weather or even critters nesting up there can cause airflow issues over time. Learned that one the hard way when squirrels decided my attic was prime real estate... but that's another story entirely. Glad you caught yours before things got expensive!