Metal roofing is a once-in-a-lifetime event, asphalt shingling is not. Steel roofing goes on just about the same as vinyl siding. As with many home improvements, the devil is in the details. The seams, flashing, caps, trim and such are the only part you could consider challenging. The bulk of the roof goes on quick and easy by either directly fastening it to your existing old roof or by laying down purlins and fastening the metal roofing to the purlins. Of course, you could tear off your old shingles, or add insulation, or make other upgrades (venting, skylights, new underlayment, etc) before installing the metal roofing if you desire. The main idea is get it right, because the metal roof will likely live longer than you will.
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