I've done a lot of caulking baseboards!
I use a clear caulk that goes on white and dries clear.
shows you where you stopped if you get back to work before
it dries.
I keep a wet cloth with me to clean the caulk off my fingers, and rinse it often.
Of course I'm caulking to stop air infiltration, not so much for looks. Still a neat job is the goal, I've never used painters tape.
If you are stopping air infiltration you seal the top of the baseboard to the wall, and the bottom to the floor.
If you don't want the caulk to show..remove the baseboard
and caulk then reinstall the baseboard.
I also caulk ceiling moldings at the top to the ceiling and bottom to the wall. as with floor moldings you can
remove the molding and caulk then reinstall the moldings.
Dap brand 50 year caulk.
Don't buy cheap as it doesn't last, and I wouldn't want to
have to do it twice!
You would be amazed at how much air leakage these two areas
contribute to the whole house infiltration.
best of luck.
Q