He has a magic sword that can, in one stroke, chop off either one head, two heads, one tail, or two tails.

This dragon is of a type related to the hydra; if one head is chopped off, a new head grows. In place of one tail, two new tails grow; in place of two tails, one new head grows; if two heads are chopped off, nothing grows.

What is the smallest number of strokes required to chop off all the dragon's heads and tails, thus killing it?

Actually, when you chop off 1 Head (your 4th swing), only 1 Head will grow, not 2.

So you'll be stuck with one head since you have no more tails to turn into heads.