Poe knew Lando before he ever met him - a dashing hero of the stories he grew up on as a kid, a constant figure in his day dreams of the rebellion. Meeting him felt like walking into a dream made real, but Poe found the man behind the myth meant a lot more to him that the myth ever could have. He sees Lando as one of the best adapted of his galaxy to earth, which given the stories doesn't surprise him at all. He's carved a place for himself on this planet and made it work for him, which Poe is both inspired by and envious of. Lando is also the firmest link he has here to his parents, and has come to regard him as extended family because of it. He hates disappointing Lando because he feels like that extends to the rest of his family - which Lando is happy to remind him of, when he's being a total idiot.