Good idea Rusty. I'll suggest that to him. Passwords became tricky here after the new owners took over couple years ago.Many sites fail to explicitly define the criteria for allowable passwords. It's nearly 2020, and you'd think that everyone would allow 50 characters, including all letters, numbers, and symbols. Some sites don't. Have your buddy dumb-down his password. If he's still having problems, have him try something really stupid, like asdf1234.
Good luck, and I hope he makes it over here soon.