Hi, I like contrast. I would paint the stair case moulding
the same color as the base moulding but leave the stringers the color they are.
Good Luck woodbutcher

I would paint the baseboard white. The darker color on the baseboard brings the floor tone up onto the wall as if it were a tile base and it muddies the contrast between the trim and the wall. You will end up with a room of off tones with no clean distinction between trim elements. I would especially warn against that because of the dark wood treads and wrought iron work.

You're right, this looks wrong...like somebody ran out of paint. The problem is that the contractor installed a nice transition, but for a situation where the stringers and the baseboard were all the same color. If you wanted that colored molding, it would have been better for the baseboard molding to continue straight over to the front of the first stair. At this point, I would vote for painting the baseboard the same color as the stringers. In the photo you have dark stairs, 2 colors of floor tile, and another color for baseboard molding; that's a little too much going on for my taste, and painting the baseboard molding would reduce the "competition."

I know this is late, but I would paint the baseboard off white. However, if you are set on keeping the baseboard color the same then I think you almost have to continue the color up the staircase moulding the same color. If you do that then I think you have to either paint the stringers the same color also (although this will make things pretty dark) or paint the stringer the color of the wall. I think leaving the stringer white will make things look way too busy.