Originally Posted by edcaya

If you're after something with loads of compartments, take a look at the various designer/non-designer baby bags out there. I've carried Rebecca Minkoff's Knocked Up tote in leather as my personal item, and I actually use the RM Luca baby pouch as a way to organize my LV Neverfull GM.

I like my Chanel Cerf (now known as the Executive) tote for its abundance of pockets, but it and Prada's own Executive tote suffer from the same problems that open totes like the Neverfull have, and they're well over $1k anyway. In your price range, I'd consider offerings from Dagne Dover, MZ Wallace, TravelTeq, Daame, and Knomo.

As for the key issue, Bobino's key clip works a treat.