installationwindows
Given basic abilities of home and car repair (i.e. installing new sinks, canned lights, basic wood working, oil changes, etc) what is the relative complexity level to install new windows, in a standard single family home ?
Does it take years of practice to be done correctly and left to a professional…or can it be studied and applied ?
Installing opening windows out of plumb (out of level), will make them hard to open and close, and may affect their ability to seal well. If the windows are fixed, this is less of a problem.
If you install them level, the most noticeable issue will be the top and bottom, probably not the sides. You can address this by being creative with casings, the molding around the windows. If you put a shallow triangular pediment across the top, it will mask the angle difference between the window and siding.
An alternative is a curved facia board at the top, or any other combination that breaks up the horizontal line.
The bottom could be handled similarly, but there is less tradition of decorative moldings or pediments at the bottom of things. A straight, stepped molding might also break it up.
SUPPLEMENT: Based on the additional information, 1/8" in one foot is not a lot of lean. I would still hang them plumb and mask it with the moldings. You could rip cut the molding on a slight angle to split the difference. Also, having the moldings NOT end at the edge of a siding board makes variances harder to notice.
The sanest thing is to order new construction flanged windows that are a bit smaller than the rough opening. Then you integrate the flange with the WRB that you're installing over the new sheathing (right?) and bob's your uncle. On the inside, you can cover up the lack of square-ness with new drywall or wood window boxes, shimmed to be square with the window, not the rough opening.
Since you're taking this house down to the studs and redoing the exterior sheathing, let me mention that you have a golden opportunity to add extra insulation outboard of the new sheathing. The marginal cost will be fairly low, especially if you're doing the work yourself and buy reclaimed foam.
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I don't think it's that technically hard. It does take some time and care. A number of years ago, I installed 21 replacement Andersen windows in my house. I was able to do about 2 to 4 a day working part time.
Replacement Windows avoided issues that putting in a "new construction" window requires. You have to deal with the exterior and interior finishes. On the exterior side, its about the flashing and waterproofing. And fitting with the siding. Inside, you have to fit the jambs to the wall, fix any insulation & drywall issues, and fit the interior trim.
Even on replacement windows, I found myself having to fix and replace rotted and failing parts of the existing window sills, jambs and trim.
The job entails attention to detail, ability to cut,shim, and fit, understand the house wrap and sealing. Eventually mounting the window level, plumb, and square.
For the unpracticed, it can be a learning curve that takes time and fiddling. But if you are persistent you will pickup speed. There are instructions that come with the windows, and videos you can watch online.