Many people who have offered may very well be experienced riders in a group/peloton, but others might not be. The last thing we'd want is a crosswind that pushes a rider into him or somebody drops a water bottle in front of him and he runs over it and topples over. Happened a few times with James Lawrence (Iron Cowboy) during is 101 Ironmans in 101 days.
That's to be decided. Still plenty of time.
Regarding training rides, we'll see how he handles the first few. If they go well and he's steady on his bike, having others along might be fun and motivating for him. Best part of rides isn't the ride, but the social aspect, right?
If you want me to let you know when we are planning on going outside, message me your cell and I'll keep a group text with whoever is interested.