Oh my gosh I just got done reading all 7 pages! Phew! So much to take in that I don’t even know how to respond!
[name]Lemon[/name], how have you not read [name]Ava[/name] and [name]Aiden[/name]? Are you for real? I pre-ordered mine on Amazon so I’d have it first thing when it came out and not have to wait to go to the bookstore! However, that was after my [name]SIL[/name] stole JJ, MM AND Cool Names. 
About hipsters and yupsters. My impression is that yupsters are hipsters that have grown up and grown out of the hipster phase. Like, the people on 9 by Design, they got older but stayed hipsters. Most people grow out of that phase, though. I mean I guess I used to be sort of a hipster. And i think my name choices still reflect that. But now I don’t dress all cool like I used to or go to rock shows and independent movies and cool coffee shops. I live in the suburbs, occasionally go see a blockbuster and make my coffee at home. I’m not a yupster though, I’m not rich enough (or rich at all, haha)… I don’t really know what I’m classified as. Anyway, I think the only reason to worry about picking hipster names is if you are ARE a hipster, in which case picking a name on the hipster list would make you already pass”, so you’d have to pick something newer and hipper which isn’t already known. So basically my point is that I think you have much bigger issues to worry about than picking a hipster name!
Did I ever mention to you that my nieces are [name]Madison[/name] and [name]Abigail[/name], almost always called Madi and [name]Abby[/name]? Well, they are and honestly? There are no issues with their nicknames being to close. It’s actually kind of cute, and I’m fairly sure that no one has ever said anything negative to their parents about it. Seriously, the only people who worry about that stuff is us crazy berries! That said, for me personally [name]Gaby[/name] and [name]Maddie[/name] would be too close, but again, I think that’s the least of your worries!
If you’re still looking for opinions, I love [name]Annabel[/name]! I prefer it tenfold to [name]Madeleine[/name], but I’m just not a big [name]Madeleine[/name] fan, popular or not. It’s not that I don’t like it, it just doesn’t have that something special [name]Annabel[/name] does, at least to me. I absolutely see [name]Annabel[/name] fitting every age. It’s a sweet name, yes, but I find it strong as well. I think you’ve moved past that worry though, right?
What does [name]Brent[/name] not like about [name]Belle[/name]? It really seems like something he’d like, it’s feminine and pretty and popular. I would push it, if I were you. And she can easily go by [name]Annabel[/name], ya know? It’s very easy to say, it really doesn’t need a nickname.
And I wouldn’t worry too much about the dog. [name]How[/name] often to do you see it? [name]How[/name] old is it? Meh… If I’m being honest, it would bother me. But i feel like you have SO many obstacles in your naming struggle that you kind of have to let go of outside factors like that.
Sorry to jump in at the end here!