I agree with your point about the coffee stop. It would be great if they let you pick a target for it. In a group ride or pace partner ride I would pick the leader or pacer. Would also be great if it let you change the target rider while it’s active. I was in a group ride and hit the coffee stop. It attached to a rider that was a reasonable choice, but then he took me out the back door by stopping to quit the event. 
Losing the Rapha kit is a longstanding issue unrelated to the update. If you contact support they can grant it to you again.
Regarding the difficulty of navigating the garage, there is a popular feature request about it. It’s been open for years but wouldn’t be at all surprised if they do work on this one.