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Question up front: On an extensive renovation, I know that it's better and easier to wait until the windows are at least framed to install siding but are there any MAJOR barriers to me removing the windows, installing sheathing and siding over the entire house (i.e. totally windowless) then, at a later date, framing the window openings from the inside, cutting the openings, and installing windows?

I'm currently working on a very extensive renovation (gutted, added second story, layout change, Plumbing, electrical, you name it). It needs the exterior sheathing and siding replaced to deal with extensive mold exposure but window placement has not all been determined. I'm doing pine board and batten.

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Windows rough openings are part of the structure of the house. With a second floor their placement and headers help hold the building up.

Making the rough openings after is much harder. It might also require an engineer to design if on a load bearing wall and with a second story above it.

The sheathing does not care if the opening is made after, quite often full sheets are nailed on and the opening is cut out after, following the size of the rough opening.

Depending on the type of siding is more complicated and should be cut/placed/trimmed around the window/opening.

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Lots of good information in crip659's answer, and plenty of unanswered questions, but it boils down to this:

The ordinary course of construction is framing walls and openings, sheath it, start flashing the windows, install windows, ensure that the moisture barrier is continuous between the window and the wall, then do siding.

It’s possible to tie yourself in knots doing things out of order, but you risk ludicrous expense and poor waterproofing at the windows (which can cause rot/mold).

If you need to strip siding/framing because of mold and leave it off for a while, just use tarps.

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