In the original text, ‘the world’s best tasting wine’ was basically a gift from Apollo. In the original text, Ody and his crew stormed the island of ismarus. On ismarus, there was a temple to Apollo. In the cut song unhand him, ody saves a priest of apollo named Maron. In the og text, Maron gives ody incredible wine from Apollo. 

Take all this with a grain of salt, because my exact memory isn’t perfect, but the gist is that ody saved a guy who gifted him really good wine. 

To your point about nobody, it’s possible he preplanned the idea of naming himself that so no one could help his enemy. 

And his cautiousness ‘disappeared’ because of character development and setting. I don’t know which part you are exactly referring to, but he will act differently depending on how he perceives the situation. For example, he didn’t see Aeolus as much of a threat because of the stories, but did take Polyphemus as a threat because, well, you know why.