We'll be painting the walls of every single room in our new (to us) Greek Revival.
The white paint on the woodwork is in fairly good shape. We have strong evidence that the wood was stripped in about 1980 by a former owner (hallelujah). There are spots where the top layer of paint is bubbling and flaking (we can see, in these spots, that there're a total of two coats of paint on the wood). I'm hoping to be able to sand these spots and repaint. I definitely don't want to strip the wood and start again.
So, now to my question: if I want a super-crisp line between wall and wood (and I do), do I need to pick out the old caulk? There are spots where the caulk has cracked, but mostly the caulk is blobby and overpainted (wall paint slopped over onto wood). It's not ultra horrible, but it is not crisp.
I've picked all the old caulk in the living room, and as I contemplate all the other rooms I am beginning to wonder if I've gone 'round the bend. What would you do? Pick it out and recaulk...or use painter's tape and strive for a new clean paint line?