Update on this issue.
Rolled the dice and decided that I'd give my Bun Burner Gold ride a shot without knowing for 100% that I solved the problem. I did change out the fuel filter just in case that was an issue, but the filter I removed still looked pretty new.
Full ride report is here:
https://www.st-owners.com/forums/showthread.php?128265-Bun-Burner-Gold-attempt&highlight=
Wouldn't you know it, but during the BBG it did it again just as I was passing through Iowa. Similar symptoms to what happened most recently. Running fine for hundreds of miles that included one fuel stop where the fuel level was less than 1/2 tank when I filled back up. The next stop was just at a rest area and fuel level was near 1/2 tank or so. Off and on the bike in less than 5 minutes and within 2 miles of being back on the highway at speed it acted starved for fuel and quit. Wouldn't initially start even with the choke on...after about 30 minutes or so it eventually fired up without me doing anything to it other than check the electrical connections on top of the tank.
The rest of my BBG to Colorado and the entire SS1000 back home 4 days later it ran without any issue. I refueled when at or just a little past 1/2 tank to play it safe and also never stopped without refueling the rest of the trip.
Fast forward to the past week. 3 separate nights I was doing some motovideo camera work 12 miles away from my house at a track meet. This entailed riding the bike to the track (no problems), running it anywhere from 2 minutes to 14 minutes at a time and shutting it off for ~10 minutes between each race. Then I rode 12 miles home on city streets.
2 out of the 3 nights when I was 10 miles into my ride home it started sputtering. Both times it had at least 3/4 of a tank of fuel.
The first time I was able to pull in the clutch, let off the throttle and coast it onto a side street with the engine still running. I was able to ride it slowly with very minimal throttle input on a side street for about a mile and then I could hear and feel the engine running normally again, so I applied normal throttle and it ran fine the last mile home.
The second time I wasn't able to pull in the clutch and coast to a side street and it died on me just as I pulled off the main road I was on. It would not fire with the choke off, but I was immediately able to get it fired back up only by applying full choke.
So...this really seems fuel related to me, right? Thoughts on how to diagnosis it when it happens so intermittently and always when I'm out on a ride (can't replicate the issue in the garage I don't think)....
I admittedly don't fully understand what the fuel relay does, but ladder106's post over in this thread sure sounds like what I'm dealing with:
https://www.st-owners.com/forums/showthread.php?127541-ST1100-won-t-start-when-hot/page8
Thoughts?