Hi ladies, I just got a preowned City and I am so in love with the softness of the leather. But the city tends to be on the small side for me (I'm a teacher so often have to bring home piles of papers to grade). I came across a pre-owned Day in burgundy and I'm contemplating if I should get that now, especially because I love hobo bags. But the thing that's holding me back (other than the price of course) is not being sure of the comfy-ness of the shoulder strap? I was pleasantly surprised by how comfortable the City shoulder strap is, even when the bag is weighed down by papers, but I'm worried that the Day wouldn't be as comfy to carry heavy since the strap is the rounded type that might not distribute weight as well. Can anyone who has both bags give me any advice? Much appreciated!