I love the group ride idea.
Really hope that in the future group workouts expand to accommodate larger groups. I would be very cool to ride with the folks from Trainer Road sometime.
I know trying to fit the video for a large group could be challenging.
One suggestion would be to maybe have a chart which graphed performance for each person in the class, but randomized the ID in the chart, so you could see how you’re doing without feeling a certain way if you’re towards the top or the bottom. The person coaching the ride could still coach via audio or video.
We did a similar thing with indoor training group this winter. The bikes were all connected to a screen at the front of the room. Each bike in the class had a number, but only the person riding the bike knew which number was theirs on the screen because it was provided on the set-up screen on the spin-bike and not to the rest of the class.
It was sort of fun, find someone who had a similar W/KG to you and make sure you kept up with their numbers or extra motivation when you fell off the top 15 in the class.
They even did an event where it the app split the class in half, randomly assigning riders to two teams, and then did 30 second sprint contests where the team with the higher watts won (the app totaled the numbers, individual stats were not shown.)