After leaving Ogygia, Odysseus is shipwrecked by a storm unleashed by Poseidon. He nearly drowns when he falls off his self made raft (or boat) because the clothes Calypso gave him only 50 lines earlier pull him down (Odyssey 5, 319-321) )
is this a) coincidence, b) irony or c) a deliberate attempt by a deceitful Calypso, whose motives Odysseus feared earlier in the book (lines 173-180). Or am I d) just reading way too much into this?
I think you’re reading too much into it. I think it would be explicit if Calypso had deliberately tried to drown Odysseus. There’s no suggestion that she anticipated the storm that shipwrecked Odysseus. And any clothes, whether or not given by Calypso, would have weighed Odysseus down the same way. Odysseus’s abandonment of his clothes prepares for the comic scene with Nausicaa on Scheria and his transformation from a naked shipwrecked sailor into a handsome, imposing figure at the court of Alcinous, and this prefigures Odysseus’ transformation from beggar to anax in his own domain.
I agree: probably d). Beside preparing for the Nausicaa scene, it’s also a realistic touch so typical of Homer that makes this whole episode more vivid. It’s difficult to swin even in modern clothes, not to mention the rectangular pieces of cloth they wore at the time. You can almost feel the taste of salt water in your mouth when you read about Odysseus’ shipwreck.
Both metaphors seem to fit the thing compared to more by association than by any literal similarity. Or to say it more negatively, they’re a bit confused, especially the second one. To me the image of Odysseus clinging stubbornly to a rock in the same way as an octopus would cling on comes to mind. However, when read literally it seems to be the pebbles clinging on to the octopus tentacles’ that are compared to Odysseus’ skin clinging on to the rock. Or is it?
In the first simile the two situations are in fact very dissimilar except for the sense of relief that accompanies them both.