The basic thing to remember regarding your roof is this: look for trouble before it looks for you. This may mean venturing up into your attic's overhead hatch or your home's crawl space once or twice a year and battling cobwebs and goodness knows what other creepy things that may be up there. But roof leaks are sneaky – they often show the bad taste of being subtle for a long time, dripping only a bit at a time so that the damage remains largely invisible if you don't bother to look. Over time, the drip leads to damage, including rot and mold that will grow quietly. If you have a chimney, particularly a brick one, pay special attention to the area where it meets your roof. If you find water seeping or draining from your chimney that is usually a sure sign that you have a leak.
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