You're not crazy. There are both "pros" and "cons" with the Lily satchels, and the bottom line is each person carries a different bag differently. Some bags work for some of us and some don't.
I actually agree with Pzold here. Initially I was not crazy about the Lily, but it did grow on me. That said, I would still only buy a medium Lily if I could not get the color in the XL size. That's why I have the camel Lily. It's actually a bit small IMO. I strongly prefer the large size. JMHO.
As for size, I carry the small laptops, and they fit fine with room to spare in the medium Lily. So I like this. It's another reason I was drawn to the Peyton or any bag with dual compartments.
I've never really had a problem with the straps on this one. It's the rope handles like the Peyton that want to slide off my shoulder or cut into my shoulder that I find annoying. These sit flat for me and are comfortable once positioned, BUT...they are definitely shorter than on the XL Lily. That might cause a problem for some people.
The thing is these satchels can expand or actually squash down when you carry them. I prefer to keep the "satchel shape", so if I don't have mine packed, I keep some packing paper at the bottom to keep the basic structure. I do this with the large Lily as well. The problem when you keep the original depth is that it causes the bag to stick out under your arm, and this is when I find that the straps sometimes slide off with a satchel style bag. This is why I have a problem with the Peyton...I do use the packing materials and don't let it squash down so much. But this bag is definitely like Pzold said...if you use it, and don't keep it stuffed, it will break in and squash down. At that point, admittedly the dual handle straps are a lot more comfy and stay put better!
The weight is definitely an issue for some people. I'm used to carrying bricks, so I actually find the medium lily to be light. This is of course compared to the large size.
The bottom line, though, is that as the other posters said, you do have to love it for yourself. It's not worth the money if you don't. I would suggest trying it around the house with your stuff in it and see how the shape changes and feels. If you wear it around for a while, then you can also assess the weight. I'm sure i'm in the minority on thinking this is a light weight bag, but it's really always "relative". I would prefer to carry a thick leather bag that looks like it's worth the money rather than a cheap light leather or pleather bag. JMHO.
Good luck on your decision, and make the decision based on what's right for YOU!
The handles on mine soften up and got more flexible after awhile. The bag got looser from weight after it broke in and I can carry my over my shoulder now pretty comfortably. It hangs much different now than it did new when it was stiff and just stuffed with paper. But I agree, for that price you have to love it!
