I would coincide them at the same ime, sections at a time if this is d.i.y.

Top down, shingles, windows, stain. If siding is stained.

Shingles, stain, windows if shingles are stained.

hendricus, I don't understand - is there a typo somewhere? Or is it just me?

Susan

"reshingling/staining"

I couldn't figure out what you meant by that so I just took a couple of guesses.

Sequence would depend on what type of windows you were getting. New construction windows would go in first, then the siding.
Ron

Oh, OK, now I get it, after rereading and reparsing:
*If the shingles are pre-stained, do the shingles and then the windows.
*If they are not pre-stained, do the shingles, then the windows, and finally stain the shingles.

They are replacement windows, and we would be stripping off existing wooden shingles and replacing with new ones and then staining them.

Maybe my real question reflects previous less than stellar experiences with contractors :o( As in, is there more risk in the shinglers dinging up the new windows and the painters dripping on them, or with the window installers messing up the new shingles.

Thanks!

Susan