I had a similar headache last fall tracking down a leak around my chimney flashing... thought I nailed it, but nope—turned out water was sneaking in higher up behind some loose shingles. Chalk marking sounds smart though, wish I'd thought of that earlier.
Chalk's handy, but honestly, it washes off too easy in the rain. Learned that the hard way... Try painter's tape next time—sticks better and still easy to remove. Saved me from losing my mind (mostly).
Painter's tape is decent, but I've had it peel off unexpectedly if the surface isn't perfectly dry. Learned that after a storm when half my markers vanished overnight... Now I use colored zip ties—different colors for old vs. new leaks. Easy to spot from a distance and they stay put no matter what. Saved me some headaches at least.
Zip ties are solid, but honestly, I find them a bit of a hassle if you're frequently updating markers.
"Painter's tape is decent, but I've had it peel off unexpectedly if the surface isn't perfectly dry."
Maybe try grease pencils instead? They stick to wet surfaces pretty well and wipe clean later without fuss.
Grease pencils aren't a bad shout actually. I was skeptical at first because they seemed kinda old-school, but after dealing with painter's tape peeling off at the worst possible moments, I'm reconsidering.
"Painter's tape is decent, but I've had it peel off unexpectedly if the surface isn't perfectly dry."
Exactly my experience. Plus, grease pencils don't leave sticky residue behind like tape sometimes does. Might give them a shot next time—anything beats guessing which leak is new and which one's been there forever...