I thought that the clip from Bonnie revealed a lot.
It looks like the Coit Tower roadblock might be TAR5 redux, with Dan & Jordan playing the roles of Linda & Karen and Jet & Cord playing the roles of Colin & Christie.
Dan is almost to the top when Jet & Cord arrive to the roadblock, and it seems like Dan is out of gas.
This would fall in line with Phil's "back and forth" comment, if the VR game is first and the roadblock is after.