A suggestion, post a new question in a new reply to the thread if you have one, don't edit your original post with a new question.
To answer your new question, yes, each individual has to provide their own receipts and records of them. There is no group. Each individual is doing their own ride. They fail or succeed on their own actions and merits, including paperwork and follow through on emailing it all in.
Remember that the really important receipts are the start and finish. The rest are documenting your route and should provide enough documentation that it was not possible to cut a corner for a shorter route. That said, make sure you have a valid receipt with ALL of the required info, and that it's legible in your picture. Electronic odometers can be a real pain at times, depending on the light conditions.
Group rides tend to have more problems than individual rides. Remember, There is no group. Your buddy needs to stop and rest, let him do it, don't waste time waiting on him when you are ready to go. The most common group failure is due to excessive stopped time because people are BSing at stops or trying to all stop at the same time.