Reddit reviews The Wrath of Klahn Crosswords: Puzzles from the World's Toughest Clue Writer
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Define "difficulty"? For some of us "It was launched the same day that 'Leave It to Beaver' premiered" is a gimme, but anything to do with sports or TV or movies or rappers is hopeless. It must be pretty (ahem) difficult to come up with a one-size-fits-all difficulty level. As a general rule you could start by doing NYT Fridays and Saturdays. The latter are supposed to be the hardest, but my experience is that Fridays are occasionally harder than Saturdays (15 minutes vs 12).
There are several published compilations of "hard" puzzles, eg Wrath of Klahn and NYT Ferocious Crosswords. I keep Klahn's in my carryon luggage for those long No-Kindle periods on flights. Some of those are 30-minute ones (i.e. reeeeeally hard).