I got a call from the dealer yesterday (really solid, no BS bike shop). No pleasant surprises for us, the dealer's techs are absolutely befuddled by this. He said they continuity tested tested every pinout, checked all the voltages, did everything in the service manual, and everything checks out 100% perfect.
In a fit of frustration they removed the fuel pump, and reinstalled it. Now it works... sometimes.
He had me on the phone and it would start randomly on various key turns. Sometimes 3 or 6 times in a row, sometimes it just got stubborn for a spell.
My dealer said his techs are out of runway on reasons and solutions - The next step would be to replace the entire wiring, hoping to isolate and eliminate a grounding issue that may or may not be present. That's where we start running into some serious $$$$$.
I'm going to give him a call on Saturday, see if the DT300 is having a 'good day', put on her clothes, roll the dice and ride her back home. I'll probably stay off the highway, as having the fuel pump cut out there wouldn't be a super fun time.
While I'm kinda happy it wasn't some obvious issue where I'd have to say 'derp' and swallow my pride, I'm now stuck with a ride with questionable reliability. Getting randomly stranded is no fun at all.
So the saga continues - If anyone has any ideas, please let me know.