I'm 99.99% certain it was the fuel pump relay. Starts right up every time now. It was actually pretty simple to diagnose once my head congestion cleared and I put my ear right down by the tank to listen for the fuel pump so the sound didn't get lost in all the other whirring and clicking my Roadie does when I turn the key on.
Phil, I thought about it being the kickstand cut out switch, but it checked out ok and at no time did the starter fail to engage.
For you Roadster owners should this happen to you: Under the left side cover there are 3 relays all in a row. Front to back they are fuel pump, engine management, and cooling fan. Since they are identical you can swap them around to troubleshoot. Obviously you want a good one in the engine management position, so swapping the cooling fan and fuel pump will get you going. I went to NAPA and bought Echlin Relay AR294 for $22.
What is it with my bike and relays? The starter relay (Echlin AR272) fried at 1000 miles apparently due to a bad harness, my Eastern Beaver low beam relay failed, and now this. Weird.
On a related note, how lucky am I it broke in my parking lot instead of East Jesus, Wyoming? At night. In the rain. It's good to know too a simple parts swap would have got me going. Eventually.
Blastedbones, I'm going to heed your warning and check that wire you mentioned as a preventive measure. And you're a better man than I, Gungadin, pushing a Rocket up a short ramp into a lifted pickup. No way in hell can I see myself doing that.