Ken, the window guy, came out yesterday to measure the kitchen. Sorry I didn't take any pictures of that, but I was wrangling the dog. Anyway, he explained to us that ripping out all the trim isn't necessary. What happens for old houses is the window manufacturer will cut off the nail strips (the little trim that you would normally nail or screw into the 2x4s). This is obviously very easy when building a new house because there's easy access while the siding and trim aren't yet installed.
So we take off that first piece of trim, pop out the sashes, cut the rope, let the pulleys drop, insulate that empty pulley space, slip in the new window, push it against the outermost trim, cram a wedge under the window (because our sill is angled), caulk 'er up, nail that first piece of trim back on and call it good! Sounds so easy.
It'll look a little like what "the boys" on This Old House are doing on their "How to replace a window" section on the handy website.
If you haven't visited the This Old House website, I highly recommend it.
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