This is me jumping up on my soapbox again: Here it comes—my fury (fury is probably a strong word) at demolition done wrong. Whether it’s a roof or interior trim, a house comes apart best in the reverse order it was assembled. To wit:
I’ve seen many a carpenter and DIYer removing baseboard by trying to take the base and shoe molding off all at once.
Not only is the base nailed to the wall, but the shoe is nailed—most likely—to the base and to the floor. And it is caulked to the wall: Triple-stuck.
The solution is easy. When undertaking a trim removal project—and upgrading trim is an primo room upgrade—the idea is to take laps of the room, removing as you go. Start with the caulk. Pierce the bead by cutting it with a utility knife. Next, pound the teeth of your pry bar in behind the shoe and pry against the base. Next, strip the base. Unless you know where the studs are, use a 1-by block or cedar shingle to spread the point-load of the bar over a wider surface and minimize or eliminate drywall or plaster repair.