There may already be a thread similar to this one - or at least some with similar entries - but here goes my attempt to collect everyone's similar thoughts under one banner.
It took me a while to notice these things, and I admit it was EON's decision to change CR's game from Baccarat to Poker that helped me realize the flaw in MI6's (read Fleming's) original plan:
Bond did not have to go head-to-head with Le Chiffre, challenging him with one 'Banco' after another. That just made him Le Chiffre's sole target after the game (as it had to be for the sake of the story). All he had to do was go 'Avec' every time, which invited the other players at the tableau to make up the difference. Every time Le Chiffre lost, half the stake would go to Bond, and the other half would be divvied up among the other players. Kidnapping Vesper and Bond would only recover half the money Le Chiffre needed to replace before SMERSH caught up to him. The rest would be scattered to the four winds.
As I already said, though, that would put paid to the excruciating climax of the novel (besides, given the losing streak Bond hit, the other players may have been discouraged from making up the difference).
The other plot device that bothers me (at the moment) was Wint and Kidd outbidding everyone in the Queen Mary's salon for the right to reserve the High or Low field for the next day's anticipated run. Everyone was taken by surprise by their choosing the Low field, as the sea was smooth and the weather quite agreeable. Wouldn't they have saved themselves some money by letting some other sucker win the High Field, then picking up the Low field for a song? (Again, though, that would have deprived Bond of the opportunity to observe the two men, and wonder about Wint's thumb-sucking - as much good as it did him.)
So, those are my two introductory WTF? moments, which of course can be written off as 'had-to'be's' for the sake of their respective stories. Regardless, what other convoluted moments have caught your attention - either right away, or after several dedicated readings?