Regrouting countertop/backspash joint - masking tape to simplify cleanup?
Actually, I think that's a great idea, and I'd tape both faces. I'd then apply a very small bead and tool (finger) it out once. Then I'd pull the tape and tool it again. You're likely to have a few spots where you apply too much caulk, and it'll come off with the tape. Your second tooling will remove the tape lines.