Muffin, thank you so much for this thorough review -- SO helpful.
It sounds as if the J. Crew one would be super useful and "easy" for me in the sense that it would be similar to other bags that have worked for me in the past. But I think I am going to keep the Minkoff. I played around with it a bit today and yesterday and it seemed to be working. I'll get a bag organizer for it to make things a little less lost inside -- if I need to. And this way I will learn how I feel about unstructured bags, I guess. It's worth a try at the sale price.