Caulk Versus Putty on Old Casings
Overall, I typically go with a cheap latex painter's caulk. The technique I use for inside corners is to cut the tip with a slanted 90 degree chisel point, so that when the tube is at an angle of 45 degrees, the tip is totally flush with the inside corner. Then, knock off as much of the pointy tip (which is the trailing edge when you draw the bead) to give the size of bead you want - usually about 1/16". Drawing a damp finger is always best to give the caulk good contact and smooth finish. For nail holes and mitered joints that you want flush with the wood surface, I apply from the fingertip, and use a putty knife to smooth it across the grain (to follow the molding profile). By applying a little surplus, then drawing the knife in only one direction, you can usually leave the caulk a little bit high only over the holes - takes practice. It will cure to almost flush.
If in doubt, put on a little more, let it cure, then come back in two days to trim the excess across the grain with a chisel - that's why I use cheap caulk, easier to trim when dry.
From contributor R:
If you have all the casings off, why don't you adjust the jambs to be square and plumb again?
From the original questioner:
Contributor J has neatly summarized all the benefits and downsides of caulk. I tend to use Bondo for major repairs and joint compound for nail holes. Bondo for miters has proven a bad idea, so I guess caulk it is.
Contributor R, that's a good idea in theory, but the job isn't the whole house, just the kitchen, so I only took casings off one side of the doorframe. I've also learned the hard way to keep dismemberment of 100 year old places to a minimum - you never know what can of worms you'll open with what seemed an easy fix. Chipping a little paint turns into a disaster when the paint is all that's holding the decayed plaster together! Yeah, the wall should be repaired, but it isn't what the customer signed on for.
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