Replacement windows
This is the type of situation that can range all over the spectrum of the carpentry world. If all the old windows are identical in size, this will make purchasing the replacements more reasonable, however, if the ten windows represent ten different sizes then the cost will reflect this. Even little measurement differences will make a difference in price. Then, too, you have to consider the condition of the rough openings when you remove the old windows, and the sills, etc. New windows will undoubtedly be true and square, and the rough openings may not be.
I hate to be a wet rag on your project, but I would tread very slowly, and do a lot of homework before I picked up any tools. You may find the need to replace a board or two along the way, and some flashing, and caulking, and shimming. All of a sudden $4000 complete doesn't sound so bad.
I wish you the very best of luck, keep us posted.
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