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Just throwing this out there as a possible option:
If your a machine nut like me and have the coin to drop then maybe look at one of the Woodmaster planer/mounders. It is my understanding that Woodmaster has good service and will actually make custom knives for their machines if you send them a piece of the old trim. It won't be as inexpensive as farming the work out to a pro but you will have a combination machine that will last a lifetime!! And there is somethng to be said about doing it yourself. I don't know about other folks but I take a bit of pride in being able to do my own work when I can.......

Besides, this is that perfect opportunity to use the old "well if I just had this machine, I could do that for you honey"!!! That's my excuse about half the time LOL.
 

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If you're not going to go the proper machine route, I would lean heavily into the farm it out as others have suggested. It is almost for certain that no matter how careful you are, some of the moulding will be damaged in the process of removing it or stripping. One other way to strip paint is to sandblast (or soda blast maybe). I have never done it in place but that might even be possible?? The same argument applies, it is more expensive to farm it out but less work (you decide). Based on your description it sounds like a major job for little gain to reuse the old moulding.

And since your working 12' up you might want to consider a roll around scaffolding. Far more stable and easier to work from than a ladder!!
 

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That’s the problem with buying older homes. By the time you start trying to remodel, you end up breaking things you need to replace. ”Ballew Saw & Tool,Inc“ will make you cutters. Just not sure how far you your willing to go to get the match.
Yep, I have thought many times I would have been better off to tear this house down and build brand new!!! Probably cheaper too! And absolutely better built!!

Remodeling is almost always a comprise between what is there and what you would like to have!
 
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