I just had new windows put in. I would like to trim them with oak trim that I can make in my shop. My concern is that it will be to rigid to follow imperfections in the wall like trim from the big box stores. Any ideas or thoughts? Am I over thinking it?
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Store bought trim will be just as rigid as homemade. The only thing store bought trim does is cut a wide, shallow rabbet on the back side, to help bridge bumps. But the one they cut is so shallow that it does almost nothing.
This is what caulk was made for.
Yes, nothing says fine woodworking like half a tube of white caulk between your oak trim and a painted wall.
Use a strait edge to see how bad the walls are. You might get lucky.
If they're bad just scribe them to the wall contours. Cutting that dado in the back side of the trim will make the scribe much easier. I just did this to a super curvy wall. You'd be surprised how much curve you can make disappear.
Oak trim is still flexible... Not as flexible as pine or MDF, but you can tweak it some.
Cut a cove on the backside. I've installed shopmade trim before and wished that I took the extra time to add the cove. https://www.finewoodworking.com/2020/02/03/how-to-cut-coves-on-the-tablesaw-2
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