I know that motorcycle helmets need to be replaced every three years. Also if you ever get in a crash with a helmet or if it gets dropped from up high it needs to be replaced. The foam inside of the helmet gets old and in a crash it will be effected and won't protect you like it should.
I would say that it would take a day or two. It's just a one day ride so really he just needs some sunscreen, comfy gloves, a riding rain suit in case he hits some rain, water and a good riding jacket. I know older guys who take all kinds of trips. If he takes several pit stops to get up and...