Measuring twice sounds good... but sometimes I think I measured three times and still messed up.
- Same here. I double-checked everything and still had one window that just wouldn’t fit right. Ended up shaving the opening a bit, which was a pain.
- Wish I’d known how much old paint and caulk you have to deal with before you even get to the install part. Took longer than the actual window swap.
- Definitely underestimated cleanup—dust everywhere, even with drop cloths.
- Noticed my trim didn’t go back on as clean as I hoped. Had to buy extra filler and paint.
- Agree it’s doable, but “not quick or clean” is spot on. Even with patience, stuff goes sideways.
If I did it again, I’d budget more time for the prep and finishing work. The measuring is only half the battle—getting everything to line up after demo is another story.
The measuring is only half the battle—getting everything to line up after demo is another story.
Can’t agree more. I thought I did everything “by the book,” but my 1950s house had other ideas. Turns out none of my window openings were actually square, so even with careful measuring, I ended up having to fudge things with shims and extra caulk. Prep took way longer than I planned, and reinstalling the old trim was a bit of a lost cause—ended up replacing most of it. If there’s one thing I wish I’d known, it’s that nothing in an old house is as straightforward as it looks.
If there’s one thing I wish I’d known, it’s that nothing in an old house is as straightforward as it looks.
Funny, I actually had the opposite experience with my 1948 place. I was bracing myself for all kinds of weird angles and hidden surprises, but somehow the window openings were mostly square—at least enough that the new windows fit without too much drama. Maybe I just got lucky, or maybe the previous owners did some work I don’t know about.
That said, I do wonder if sometimes we overthink how “off” old houses are. I mean, yeah, there’s always something unexpected, but a lot of it can be worked around without replacing everything. I kept most of my old trim by patching and sanding, even though a couple pieces were a little warped. It’s not perfect, but I kind of like the quirks.
Curious if anyone else managed to reuse their trim or if I’m just stubborn. Sometimes I feel like I’m the only one not starting from scratch every time something’s a bit wonky.
I get what you mean about not everything needing to be replaced, but I actually ran into a lot of trouble trying to salvage my old trim. My place is from the early 50s, and the wood was so brittle that even careful removal led to cracks or splintering. I tried patching, but the end result looked off, especially next to the new windows. Maybe I just didn’t have the right tools or patience, but in my case starting fresh made more sense. Sometimes character is great, but sometimes it just feels like extra work...
That’s pretty much what happened with my place too—the trim just crumbled when I tried to pry it off. I get the appeal of keeping original stuff, but how much time are you supposed to spend patching and sanding before it’s just not worth it? I always wonder if the “character” is really worth the headache, especially when new windows make everything else look tired. Did you try any special tools or just the basics? Sometimes I think the old wood just doesn’t want to cooperate, no matter what you do...
- Totally get where you’re coming from. Sometimes that “character” just feels like extra work, especially when you’re knee-deep in dust and splinters.
- I tried both a pry bar and a multi-tool, but honestly, the old wood just split no matter what. Some pieces just aren’t worth saving.
- I ended up mixing new trim with some patched originals—didn’t look perfect, but once everything was painted, it blended enough for me.
- At some point, it’s about sanity over sentiment. Nothing wrong with making things easier on yourself.
At some point, it’s about sanity over sentiment. Nothing wrong with making things easier on yourself.
Totally agree with this. I used to stress about saving every bit of original trim, but after splitting a few boards and wasting hours, I just started picking my battles. Did you notice how much faster things went when you stopped worrying about “perfection”? Sometimes close enough really is good enough.
Man, this is hitting home. When I started on my windows, I was all fired up about keeping every bit of the old woodwork. Thought I’d be “preserving character” or whatever. But after snapping a couple of those ancient, paint-caked casings—and losing a weekend to patching and sanding—I realized my sanity was worth more than nostalgia.
Honestly, once I let go of that perfection thing, the whole process sped up. The first window took me forever because I was being so careful, but by the time I got to the last one, it was like, “Does it open? Does it close? Is there insulation?” Good enough. Plus, I swear my energy bills dropped almost overnight, so I stopped caring if the trim matched exactly.
I’ll admit, there’s a tiny part of me that cringes when I see a slightly uneven line or a bit of caulk that’s not museum-quality. But then I remember how much more comfortable the house feels now—and how much less drafty it is in January. That’s worth way more to me than original trim that only I notice anyway.
One thing I wish someone had told me: don’t underestimate how much old stuff is just... done. No amount of gentle prying or fancy tools will save some of it. Pick your battles and save your energy for getting those windows sealed up tight. Your future self (and your heating bill) will thank you.
This really resonates. I went in thinking it’d be all about craftsmanship, but the reality check hit fast—sometimes the old wood is just past saving, no matter how careful you are. Did you run into weird gaps or out-of-square frames? I found myself improvising with shims and foam way more than expected. Also, I underestimated how much dust and debris would get everywhere... it was like living in a construction zone for weeks. Looking back, I wonder if there’s ever a perfect balance between preserving character and making the place actually livable.
I get where you’re coming from, but honestly, I think some of that “preserving character” stuff gets overhyped. I tried to save my original sashes and frames, but the amount of rot and weird angles just made everything harder. At a certain point, it felt like I was forcing old materials to do a job they weren’t meant for anymore. I ended up just replacing the worst offenders with new units—yeah, it lost a bit of the old look, but the house is way less drafty now and actually easier to keep clean. Sometimes practicality just wins out.