Our 200+year old farmhouse had multiple additions added (1960, 1980, 2000), and we have leaks in every addition (but not the original 1790 rooms). We only saw the first leak, on a flat roof over my office, prior to buying the house-which the previous home owners professionally 'repaired' before we bought.
Since we didn't have much rain over the next 2-3 years, we didn't have a problem. Since then however, we've had buckets of rain almost each year, which let us see all the different leaks.
We had the flat roof re-done, thinking it was the roof. Since it still leaked a month later, they came back and re-did the problem area...still leaked! One of the pros told us it wasn't the roof, but where the original 3-story building met the different additions.
Any idea what we should start looking at? We'd likely hire pros to do the work, but don't want to lay out more money and not have it fixed.
You do have to look at the original roof as well. If you tell the roofer: this is where the leak is-fix it, the roofer will not argue the point. Get several roofers and ask for opinion and estimates and stay out of it. Come back with photos and estimates, at which point we may be a better help. Photo now will not help, since a house that old (or young) may have several leaks that can't be seen without the 3d observations in the bright sun light.
Facia, gutter, windows, siding, vents, obvious flashing, any openings, all can leak - if you don't know how it was installed. Additions can move as well, depending on how the attachments were done. You can have a seasonal leaks as well.
I am stating the worst possible cases, but it is better to go into it armed.
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