Ride a small block and pencil along the floor to transfer its exact contour onto the baseboard, back-bevel the cut with a jigsaw, and sneak up on the line with a belt sander — the board lands tight to the floor with no shoe molding needed.
The rule that separates clean trim from cracked paint lines: caulk belongs at change-of-plane joints (where trim meets wall), and two-part wood filler belongs at same-plane joints (seams and scarfs in the trim itself). Caulk in a flat seam shrinks and telegraphs.
Nothing reaches into a stairwell to clamp a riser while the glue grabs. A small block on the riser and a scrap of wood screwed to the tread above it make a lever that applies the pressure instead.