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2

Personally, I'd stop the crown molding at each end of the fireplace with some compound miter end caps unless you're really good with a coping saw. If you run it a couple inches off the ceiling , your recessed lights will leave a shadow at the top of the fireplace. Just my humble opinion.


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Millwork shops typically charge $100 to $500 to make custom shaper knives to match your profile. Alternatively, any cnc router can make any custom shape like that. Lastly, if you wish to, you can make a home made plaster molding to match using this technique: https://www.oldhouseonline.com/repairs-and-how-to/knife-and-mould-plaster-technique-explained ...


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The "three stairs" could be cut with a straight bit or saw (and a fence, set over multiple times) unless you are running enough linear feet to justify a custom-ground shaper bit. I'd just call them rabbets. The part above that feels like some flavor of ogee moulding from the picture (less so from the drawing, which looks closer to a quarter round.)


2

First, thank you for adding the pictures. It helps a lot. My best suggestion would be to remove the existing ~1.5" sill. (Properly speaking, it's a stool, with an apron below.) Put a new 4" or so one on. You'd probably have to remove the apron temporarily, as the thickness of the new stool might or might not be exactly the same as the old. Use long ...


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I would still do a takeoff on Michael Karas's answer about extending the door jamb and trim to the floor. I had the same situation where a new floor was installed with a much thinner material than original, so I had many gaps around the bottoms of door trim that had to be remedied. I used a small piece of three-quarter inch wood to serve as a gauge block and ...


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The better way is to extend the door side casing trim to the floor surface. Ideally that would involve removing the old paint covered trim and replacing with a new longer piece. The alternative, as you propose, to run the base shoe molding under a foreshortened casing is not going to look too great as there will still be an ugly gap due to the rounded top ...


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