That's a great story and Joe even edited out some of the more entertaining parts of the 1990 adventure, like where the pole, the flag, and the mask came from.
The first time I ran HTC was 1996 with a team of 11 other people I'd never met before in my life. Got picked up by a team that had two of their guys go lame at the last minute (VERY common occurrence BTW).
My mother-in-law lived in Seattle so my wife and I headed out for a family visit. I was to meet two of the guys who would be driving a white van at a fast-food place in Seattle for the drive to Portland. Explaining to the mother-in-law the wisdom of meeting up with strange men driving a white van to run through the darkness in Oregon proved quite a challenge. It got even more exciting when we discovered how many white vans were driving through that parking lot. Neither I nor the van drivers knew what each other looked like in any detail. We finally met up and though my mother-in-law though I was totally insane and that her daughter would soon be a widow, we took off for Portland.
We arrived a few hours before the start and had to assemble the two vans and make sure everyone was good with their running position. Three of us were late members to the team, with one late member someone's girlfriend that was filling in for someone that pulled a hammy the week before. It was decided to shuffle things so boyfriend/girlfriend were together and give me the longest set of legs (18.x miles) because I was in the middle of marathon training.
That year they took everyone that planned to run under 24 hours and put them in the last two starts, putting us in the last start going off with the elites. We were DFL for the first 5 exchanges and fortunately started to catch more people by the time our van #2 started, until the first guy in our van followed someone else off-course and went an extra two miles. We all started studying our maps harder.
Running race pace in the dark down an unmarked suburban road proved to be a bigger challenge that I expected. I could occasionally see the flash of a vest but the people I was catching were running considerably slower so it's basically running in the dark by yourself trying to push the pace.
After the van exchange we found a school that was renting floor space in the gym to sleep. A few bucks was a bargain to get stretched out on a gymnastics mat instead of leaning against the wall of a van.
By dawn we were in a mass of team vans going stop and go down the road. After we did our 2nd legs we charged forward and found a field to park in where we slept in a grassy ditch. You learn to make do. We when we got to the 3rd and last 1-2 van exchange traffic was so bad we left our #7 guy and the exchange and kept driving. Teams were getting stuck at the last van exchange and not getting their #8 guy forward in time. Sickening situation to watch your runner pass you while you're stuck in traffic.
At the finish we all gathered and ran in with our last guy. It was amazing. We were all hot, smelly, and exhausted but we hung at the party then went to find the condo we'd rented in Seaside. The condo with one bed and a couch. On the way one of the late-comers ran into some friends and wanted to stop and chat for a bit. We told him where we thought the condo was, where we planned to get dinner and left.
After we dropped our stuff off we found out the dinner place was jam packed and we couldn't get in. We found a "plan B' nearby and some of us took turns going back to find our lost teammate. No sign of him. We hunted for him after dinner, he's not at the condo, we don't have a cell number. The team captain has his home number, no one home. We hunt some more but have to get some sleep.
In the morning we remember his stuff is still in the van and call his home number again. BINGO! Turns out he couldn't figure out which condo, or find the van in the sea of white vans, so he called his Dad who drove down from Portland to pick him up. We met up with him on the way back to Seattle and gave him his duffle-bag.
Never saw any of the people again.