Are you not considering the Re-Edition 2005 w/ the guitar strap + chain because of the price or simply not into the look?
I have that one in nylon and personally, to this day, I think it's the best choice I made when I was purchasing the Re-Edition series. That bag to me is like a 3-in-1; I can wear it crossbody, as a shoulder bag and more...and of course I LOVE the overall look of the bag with the thick strap and all.
BUT! If that look isn't for you then I get it. In that case, I would spend a little bit more ($50CAD+) and get the Re-Edition 2005 mini w/ leather trim. It gives the bag a more luxurious feel, which can be dressed up easier, and I believe will retain better value and life in the long run.
IF you don't mind the thick crossbody strap+chain look, have you seen
this one?
View attachment 5092199