I think the Masterpiece Caliborn is the same as the one who becomes Lord English. We know that SBAHJ is a form of subversive media used against HIC's rule, and my theory is that it works by mocking Caliborn's DeviantArt phase, a phase which he would like to forget. The Condesce probably doesn't like being reminded about how much of a tool her boss is, either. Caliborn just -acts- surprised when the heroes show up to kill him, because failure to do so would cause an unstable time loop.

I mean, Caliborn is the Lord of Time, he doesn’t bend to the Time Loops of the Alpha Timeline, the Timeline bends to him to form Loops that favor him, which is why him being forced to act surprised doesn’t quite cut it for me. Also, SBaHJ is just Dave’s style- Rose uses lengthy prose to the same effect, and they’re jabs at Condy, not English.