What to replace first - roof, siding or windows (in what order)?
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Roof first especially if tearing off old one, then windows which effect placement of new siding against the window trim.
Agree
Roof, windows, siding, in that order. If your roof is bad then new siding isn't going to be safe when it rains. The rain will leak down into the walls and bye bye dollar bills spent on siding. When it comes to windows vs. siding in the replacement arena, it is windows first because they may end up being smaller (or larger) than they are now and siding must be cut accurately up to the window frames' edges. You don't want to put in siding first and have them have to cut through it to replace window frames, etc.
Agree
Roof!
roof first. then windows and finally siding