Good Question. I like the hobo because i like the slouch but hobos are hard to keep organized and locate things in. I like the gallery tote b/c its organized but too structured and boxy. hmmm... did I answer my own question?
I vote for the gallery tote, as well. I just switched my work tote yesterday from my Legacy satchel to my Signature gallery tote and I absolutely love it. I've always loved the gallery totes and never much cared for hobo styles.