HELP Replacing PELLA Windows c.1986

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BigB1990

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Hi, I’m looking for some advice on how to deal with replacing the Pella windows in my house.
I’ve installed many replacement windows in my Mother’s house with no problems, very old single hung with the old weights. I’m now looking to do my own and am not sure how to proceed. I’m not even quite sure how I need to measure for these windows. They are PELLA aluminum clad windows from about 1985 or 1986.
I am attaching a couple pictures to help show what I am talking about. The windows are wood with aluminum cladding on the exterior and have a vinyl jamb cover. With the cover removed I would assume I would need to remove all springs, aluminum weather seal etc. back to the wood frame. This is where I would want to measure the width. There are a couple problems with this.
1) As you can see the aluminum clad on the outside of the window sticks out well beyond the wood frame.
2) The bottom sill lip does not line up with the inside stop. This lip is wrapped with aluminum.
I would like any help I could get before I even measure and order for these replacements. I’m planning on replacing 10 of these next (2016) summer. Hoping I can find someone who has dealt with these Pella windows and can give me some guidance. Where do I take my measurements and how will the replacements slide in (what do they stop up against)?
Thanks.
20151224-Pella Windows-c1986-0005.jpg

20151224-Pella Windows-c1986-0004.jpg

20151224-Pella Windows-c1986-0001.jpg
 
I'm not sure I made it clear in my original post that I am looking to install vinyl REPLACEMENT windows in my Pella frames.

I am hoping I will not need to remove my siding and complete window frame and install new construction windows.
 
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