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Had pretty much the same experience last spring. Thought for sure it was the crown (it looked rough), but nope, flashing was the culprit. Ended up sealing it myself—used step flashing and a good quality sealant like you mentioned. Also, quick tip: check your attic insulation afterward. Mine got damp from the leak and I had to replace a small section to avoid mold issues later on...just something to keep an eye on.
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