A few observations maybe worth mentioning...
I'm using a stereo piezo system feeding into an onboard pre-amp (much smaller and simpler than yours). Plus I have a mounted mic. The point being, I have relatively short cables running all over the place on my DB.
Once a pickup system and a pre-amp is mounted, the next worry is that the cables don't rattle. Some of them I use double-face M/F Velcro to secure, some of them I use zip ties to secure, and some of them I just snake through various points on the tailpiece, under the fingerboard and elsewhere on the DB to secure.
I'm very lucky to have a weird but very functional custom A-frame tailpiece, made by one of the Deuce Bridge builders, and equally off-the-wall looking as their bridge is. This tailpiece provides me with places to mount my 3 plug sockets, in addition to acreage on which to route and use up extra cable. Doing all of this with a standard tailpiece might be a lot more challenging.
In my situation, I also mount my pre-amp on the back side of my bow quiver. It's a small, simple K&K Dual Channel Pro ST, and the mounting is extremely solid, necessary volume and blending knobs are easily accessible, and I can also easily pull the back off the pre-amp to change batteries or settings inside the box.
Looking at the Headway EDB-2 HE, I'm hugely impressed with everything it offers, but it's a huge piece of machinery. It makes me wonder if perhaps a lighter, simpler, more mount-able pre-amp might be a better answer, and then going wireless from that into your Headway, or perhaps even going wirelessly directly into your amp or FOH. Personally, having had only 2 knobs to worry about on-board my DB has been distracting enough.