I think this design has a lot of potential. I have minor issues with some parts of it, but it more than meets the requirements for my casual EDC use case.
Of course, the real star of the show here is the VX11 fabric. I love having the face texture of cotton canvas, but with sturdy ripstop and a stiffer, crinkly laminate hand underneath. I'm almost tempted to wax the canvas just for the patinated look and feel, but of course that's not actually necessary for weatherproofing thanks to the laminate backing. I can't wait to see how this fabric will break in over time. I hope DP will eventually offer it in more colors, as receptiveness to dyes is one major advantage that cotton has over your typical synthetic sailcloth face materials.
I hope you'll do more with this fabric in the future - this marriage of heritage and technical fabrics feels like a great fit for Waterfield in particular.
I also like the lining material, which feels much sturdier than the glossy, low denier ripstop nylon liners that some other brands use. The color is good for visibility without being obnoxious retina-searing fluorescent orange.
That said, the construction of the liner is the first of my nitpicks about this bag's design. The liner is only anchored to the shell around the mouth of the bag. This will be good for cleaning, since the liner can easily be turned inside out. But when the bag is only lightly filled, I feel like I'm digging through a sea of loose fabric to access the interior pockets. Anchoring the bottom corners of the liner would make the bag feel neater and nicer to use, IMO.
I'd also love to see a zippered slash pocket in the main interior compartment for flatter items like a wallet.
Next, I find that the shallow quick access pocket that's housed inside the top flap is both the coolest and most awkward feature of this bag. I haven't personally had issues with small items falling out of it, but it does sometimes get in the way when I'm trying to get to the main compartment while wearing the bag on my side (this is also partially due to the aforementioned loose liner fabric). I imagine a simple snap button or magnetic closure could help alleviate this while still affording quick access.
Housing this pocket in the top flap is a really cool use of space, but it does make accessing the front exterior pocket take some getting used to. When I grab the flap to reach into the exterior pocket, I'm gripping whatever is inside the flap - earbuds case, chapstick, pill case, etc. Maybe a small webbing loop or flat handle on the underside of the flap could make it easier to manipulate without disrupting the outer profile of the bag.
I'm happy with the front exterior pocket as-is. I'm not worried about things falling out during normal EDC use, and I mostly use it for things that are attached to the daisy chain under the flap anyway (great feature, btw). If this were a travel bag, I'd want some kind of closure. But for EDC, I prefer the quicker access that an open pocket provides.
Finally, I've often found myself wishing that this bag had a top handle for easier on/off and quickly moving the bag around without fully putting it on. A simple flat webbing handle on the upper back area would be a welcome addition, and wouldn't clutter up the clean profile of the bag when worn.
With those adjustments, I think you'd have a real winner on your hands. Maybe a small-medium crossbody bag like this is kind of niche, but I find it's just the right size and form factor for days when I'm not carrying my laptop.