We recently purchased a home built in the early 1950's with an addition put on in the 80's. We're hoping to remove the vinyl siding and replace it with some kind of stone and increase the insulation next year, but in the meantime we want to replace the original windows (some wooden sash from the 50's and some aluminum sliders from the 80's) in our childrens bedrooms before winter.
We'll likely hire a carpenter to do the job, but I'm wondering what considerations need to be taken to ensure that the exterior work next year won't be odd looking, difficult or more expensive than necessary.
Since you are replacing the siding, installing foam insulation boards under the new siding is your best bet. The biggest concern with the new windows would be the width of the jamb and the depth they are set in the framing. You need to factor in the new wall thickness with the insulation and stone covering. The other thing would be the moulding around the window, with stone, brick moulding is the most popular.
The biggest problem you will have is sealing up the windows untill you get around to replacing the siding, since they will be sticking out from the house.
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