Need advice on replacing an old leaky roof

Good catch on the ceiling stains—those can definitely sneak up on you. Another thing to consider: have you checked the attic insulation yet? Sometimes leaks soak into insulation first, and you won't notice until mold sets in...speaking from experience here.

Yeah, attic insulation is a sneaky one. When we first moved into our custom build, I thought I'd covered everything—until I noticed a weird musty smell upstairs. Turns out the insulation had been quietly soaking up water from a tiny leak near the chimney flashing. Didn't even see stains at first, just that funky smell. Definitely worth poking around up there before things get moldy...trust me, mold remediation isn't cheap or fun.