The starting point on the dime, at the bottom of FDRs neck, only touches the big circle 3 times - once at the top, once after 120° and once after 240°. However, we're not talking about how often FDRs neck touches the big circle. We're talking about how often FDRs neck is at the bottom of the dime. At 90° along the big circle, FDR has only rolled 3/4 of a full revolution. But it's ALSO rolled along 1/4 of the big circle's circumference. So FDRs 3/4 rev + 1/4 rev from the big circle means FDR has traveled 360° total and is now right-side up even though it hasn't yet made contact along the dime's full circumference.
At the bottom of the big circle, FDR has rotated 1.5 revs + .5 revs from the big circle. That's two total revs so now the top of FDRs head is against the big circle but he's right-side-up from our perspective.
At 270° along the big circle, FDR has traveled 2.25 revs + .75 revs from the big circle. The back of FDRs head is against the big circle but he's right-side-up from our perspective.
At 360° along the big circle, FDR has traveled 3 revs + 1 rev from the big circle.