I also just up sized my bag,.
I'm coming from a Thule Perspectiv Compact sling which is a great compact bag that can hold up two cameras like an A7 (with a smallish lens like the 55) and an A6000 at a time. I use mine as an EDC (everyday carry), so it needs to carry random things in addition to the camera/cameras and lenses so have mine carrying an A7RII with 35/1.4 with a 24-240, as well as a few other random things. I added a Tenba shoulder pad to it and it has been serving me very well for some time. It can also be worn around the waist, though I used it primarily slung across my shoulder. Even though I decided to get something a bit bigger (to accommodate larger lenses if needed, and enjoy the additional flexibility the added volume would afford) I'll continue to use the Perspectiv when I need something compact.
I just received my Peak Design Every Day Messenger bag and I have to say it has exceeded my expectations. I was pretty iffy about ordering one of these as they seem kind of expensive and wondered about the hype (most reviewers really like this bag) versus reality of this bag.
The material and build quality is often praised by reviewers and it seems like well deserved praise. All of the materials just feel very durable and of a high quality, and they are put together very well. It definitely feels like a high end product.
The various innovations (like the re-shape-able dividers, Capture integration, adjustable latch, streamlined quick adjust strap, etc) seem genuinely useful (I was concerned that they would be over designed gimmicks), and I appreciate that they are quite functional.
I haven't fully figured out how I want to configure the interior, but it has been a fun exercise to rapidly go through a few different configurations simply by flipping and folding the dividers in various ways (without having to undo and re-seat Velcro every time).
I've currently got it packed with everything I used to have in the Perspectiv + a NEX-5R, with room to spare. A big challenge for me will be to resist the temptation to overload the bag, as it can expand to hold more than is probably healthy for one's back when slung on a single shoulder.
If I had to criticize the Everyday Messenger, it would have to be regarding pockets. I kind of wish there were more of them or that the two side pockets it comes with were more useful. As it is I will probably end up only using them to store random unimportant things or trash.