Started the day at the Black Butte Trailhead at 6:50am following a slight delay due to thunder storms. Ran up to the summit of Black Butte arriving at 8:23 am. Took a quick pic at the summit then headed down arriving back at the trailhead at 9:09 am. Took a leisurely transition to grab food, recover the legs a bit. Departed on my gravel bike at 9:29am headed on the base loop to avoid the highway road section. Loose, sandy gravel with some down trees took slightly longer than expected, but once I got onto the road and main scenic bikeway pace improved. Finished the ride at 12:44 pm in the Skull Hollow parking lot where my wife and friends were waiting. Took another slow transition to get in some food, then headed out for the 2nd run with my pacer/friend Taylor at 1:10 pm. We arrived at the summit of Grey Butte at 2:10pm and could see a thunderstorm headed our way. Grabbed a quick pick and headed back down. Arrived back at the parking lot to finish the adventure at 2:54pm for a total time of 8 hours 5 minutes. Roughly 4 hours moving time on feet and 3 hours moving time on bike, and an hour of transition and general faffing.
Really fun challenge that could definitely be done faster by someone using different bike choice, and way faster transitions. If you were willing to ride the highway for a bit a road bike would definitely be faster on this course. Wearing a trisuit or some other clothing setup to avoid transitions would also speed things up.