I had a hard time buying Jean-Luc Picard as a hard boiled PI, but I suppose that's the point of a holodeck program- you get to fantasize about being something you aren't if you want to.
Picard being a fan of the Dixon Hill novels, on the other hand... that seems out of character.
I know a guy who is a literature snob and is probably the last person I would have expected to really get into Raymond Chandler novels. Anyway, he was raving about those books so I read a few. It turns out that Chandler was a phenomenally weird wordsmith. Inventive, funny, and unexpected. If you're looking at midcentury American writers, Chandler is hugely underrated. Maybe in a few centuries he'll get his due.
Sure, it's detective pulp. But it's detective pulp that's been given a strong hallucinogen and whacked over the head a few times before waking up in the desert.
Eh, I have to admit, I have a hard time buying it, too. This is a guy who reads Shakespeare in his spare time, not trashy, pulp detective novels from the early-mid 20th century. He even thought taking a trip on The Orient Express would be too indulgent. Picard liking Dixon Hill novels makes no sense. Just like off-roading in an ATV.