I'm going to go against the grain and suggest you not start with a series book at all. Try one of his standalone novels written under the name Carter Dickson, like 'Fear Is the Same'. It's a historical swashbuckler with a mystery element. This lets you appreciate Carr's sheer storytelling skill and prose without any series baggage. If you enjoy his writing voice here, you'll be more inclined to push through the occasional slow patch in his more famous puzzle-centric novels. It's like a palate cleanser before the main course of impossible crimes.
His short story 'The Shadow of the Goat' features Henri Bencolin and is a perfect little locked-room tale. You can find it online or in various anthologies. Read it. It'll take you 20 minutes. If you finish it and don't immediately want to know how he pulled off an even more complex trick in a novel, then maybe this isn't your genre. But if that little spark of 'how on earth...?' ignites curiosity, you'll know you're ready for the novel-length treatments. It's the most efficient litmus test.
Look at the dedication or introduction in modern editions. Sometimes editors or fellow mystery writers like Martin Edwards will point out which book they think is the best intro. That's a credible opinion from someone who knows the field intimately. If the new edition of 'The Judas Window' has an intro by a contemporary crime writer praising it as the perfect locked-room novel, that's a strong signal. Use those paratexts as guides. They're written for exactly your situation—a new reader looking for a way in.
Carr's work can be divided into 'Golden Age' pure puzzle and later books that incorporate more thriller or romantic elements. If you're a pure puzzle fanatic, stick to the 1930s and 1940s output. 'The Arabian Nights Murder' (1936) is peak puzzle. If you like a bit more adventure and drama mixed in, his 1950s books like 'Scandal at High Chimneys' might appeal more. So your starting point could be chosen based on which side of that line you think you'll prefer. The early ones are denser with clues; the later ones are sometimes smoother reads.
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It's interesting how his reputation has fluctuated. In his day, he was a bestseller, the go-to for impossible crimes. Then he fell out of fashion as gritty realism took over. Now, with the resurgence of interest in classic puzzle plots, he's being rediscovered. The 'key' books are key not just to his career but to an entire, almost-lost subgenre of mystery that valued ingenuity and escapism over violence and procedural detail. Reading Carr is a conscious step into a different, more playful era of crime fiction.