Thank you, I'm sort of getting more and more excited.
With Tracey, I'm happy for them to have a casual sort of acquaintance, having been at Hogwarts at the same time for a couple of years. Same with Flynn, though I can't seem to read his bio - link seems broken or something - so I don't know much more about him. He relates well to most Quidditch players, though, especially if they're Purebloods or supporters.
With Annabelle, her crazy might put him off a bit, but if it came to it, he'd probably pick siding with her over having his throat slit :P
He does drink a lot, and sometimes prefers the anonymity of Muggle pubs, so that's a possibility. Having trouble with her link, too, so couldn't really tell you how they'd get along.