On handling drop cap Qs in the London Review of Books:
We tried replacing the Quadraat Q with a Q from another typeface but couldn’t find one that worked well. As Quadraat is in all other ways exemplary, the imperfect but more-or-less satisfactory solution was to make an adapted Quadraat Q with a shorter tail that doesn’t extend quite so far vertically, and not at all horizontally, from its allotted space.
Try tackling this sort of problem on the web. Drop caps were all the rage ten or so years ago, when we very keen to explore magazine and book type online. You don’t see them very often now; partly, I expect, because of the sheer difficulty and going-against-the-grainness of implementation, and partly because we’ve probably just accepted that the malleable, fluid and formless web isn’t print.