Oh, go for it! Its not too hard at all. The worse part is simply getting the tape on perfectly straight. Especially if one has a stern with a long overhang (as we do). If one has a reverse transom its much easier of course.
There are actually boot stripe paints made (I recently discovered this), you can also use a regular topside paint OR even use a bottom paint like one of the Petit Vivid paints that come in multiple colors some of which don't have Tin or Copper just the biocide.
If it is a very narrow boot stripe you could consider using the boot stripe tapes rather than painting. Or, get clever and paint a wider boot stripe and use on the contrasting color tapes to accent it.
Keep us informed as to what you do