Another vote for horizontal
Although I just ordered a Ristretto (olive/cayenne, so it won't ship for a couple of weeks), which has a vertical orientation, I vote for horizontal for a mini-cafe bag. That's the depth of the leather shoulder bag I carry daily, and I've found that it is so much easier to find and retrieve objects in it. I rarely lose items in it, whereas I always lose things in the deeper bags I own.
If I might also cast a vote for more O-rings: I love the organizer pouches and key fobs and have several of each. But unfortunately, there's only one O-ring in my ID, and I think that will be true of the Ristretto, too.
Finally, I guess I'm in the middle in the great pocket debate. I like having organizer pockets in a bag, but I agree that when there are too many, it's easy to lose things. I once lost a watch for an entire year in the depths of an LLBean bag my mother gave me. And even a few hours after I packed it, I could never remember where I had put things in it and wasted a lot of time searching. That's the main reason I stopped using the bag, so I do know that too many pockets can be a bad thing. But so can too few!
Thanks, Tom, for asking what we'd like to see. I can't wait.