I know lets design the satchel with one compartment then you have the best of both strap, handles and one compartment. There that was easyI personally love the hobo (I get too confused with multiple compartments!). I suppose you have to weigh the pros and cons of each bag. The hobo--one large compartment, comfortable on the shoulder, 1 strap, roomy, etc. The satchel--multiple compartments, 2 handles and 1 shoulder strap, etc. My vote is the hobo, but the satchel is definitely more versatile. Good luck deciding and let us know what you end up doing.