Kcoach, I have the black hobo and black daily as well. I struggled with deciding to get the black daily for the same reason you are struggling, but in the end, I grabbed it because I thought I would regret not doing so later, and now I'm glad I have both....the daily stores so easily, packs well, beautiful leather, etc.....but I love love love my hobo in black and love that hardware with it. Honestly, I would keep both. I also feel like they are very similar but am so happy with both of them that it makes sense. I do think the hobo is a bit dressier because of the hardware, and the hobo strap is a little more comfortable when I am carrying a lot, but the daily is just too smart a purchase not to stick with it. The Preston is really cute but if forced to get rid of one of three, I'd probably get rid of the Preston.....but if you can keep all three, and the desire to shed is merely due to overwhelm, I would keep all three, because they are all really nice. Just can't go wrong with black, and these will last forever.