I have sold several due to the weight - like the Plaza bag. I recently got a court but I haven't carried it on a long trip yet. A lot of my bigger vintage bags have wider straps, like the kind on Rambler's Legacy. TBH, almost all my bags will hurt my shoulder if carried for a long time. I always have trouble finding the right bag to take on a trip when I know I'm going to be walking for a long time.
Have you ever tried a daypack? If Im going on a long outting, I usually take my Herschel backpack & it distributes the weight comfortably. Now that I have a coach daypack, Im really looking forward to long outings so I can test if it’ll be just as comfortable