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It seems to me that the two basic issues with Making History are that it deals with an established trope (stopping Hitler) and that it needed a good editor.
It's hard to play with a tired trope, but that doesn't mean that it can't/shouldn't be done and to be fair to Fry, I don't even know that time travel tropes in regard to Hitler were nearly so well identified when he wrote this 20 years ago as they are now. Moreover, playing with the trope can be done successfully, as with Kate Atkinson's Life After Life and Dicks's The Man in the High Castle.
The good editor, though.... If the book had been subjected to even semi-rigorous editing, that would have have cut the self-indulgent bits, the tedious (did we really need the entire Gettysburg Address?), and the illogical, and trimmed it to about 400 pages, this might not have been an entirely successful treatment of the subject, but it would have been a much better read.
I think it's partially authors who are too big to edit, no matter what, and also that editing doesn't pay in that it makes no difference to end sales. Oh, for the days of Maxwell Perkins!
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