What's your preference for carrying style (hobo vs satchel), and for hardware (silver vs gold)? Also, are you a big bag girl, or more of a medium bag girl?
If the designs both appeal to you equally, I think you'll probably need to look at practicality and how well the bag suits your personal preferences for functionality. If you get a bag in a carrying style or a hardware colour that you don't like, or if you get one that is too small/too big for your typical usage, you may find yourself just storing the bag away rather than actually using it.
BTW, size-wise, I think the Venice Hobo is definitely larger than the Howard St Satchel, which is probably best classified as a medium-sized bag. (It seems to be comparable in size or slightly smaller than the Trigger Medium Satchel, for instance.) Luna Boston has dimensions of the Howard St Satchel up, and the tPB video with Monica shows her handling the Howard St Satchel too, to give you a sense of scale. HTH!