....and I am sure this was covered many times in the beginning but to add my voice for no reason at all: If you are a USA Cycling club then you have club insurance that covers members when participating in official club activities like rides. This club obviously wants to cross their T's and dot their I's so requiring a waiver to be signed by anyone who isn't a member of the club will extend the coverage on them for the event even if it isn't a permitted non-competitive.
As for jersey - wear a top. If it's a bunch of Roadies then I wouldn't be surprised at all if they required shoulder coverings as that is required to take the start in any USA Cycling road event. I would never require that myself..but...
yeah - hybrid riding, flat bar, no shirt, no helmet wearing rider who wrecks... sounds like a great troll thread but regardless I would also invite that rider over to my shop so I could talk to them about why some things are done certain ways. I would loan gear and invite them back. If it kept up i would ask them not to join in the future. For reference I have never asked someone not to join our ride or not to come back.
For the record all of the A-holes who left in the past left on their own. I didn't have to ask them.