This is a really good point. I'm surprised the box office cannot print it for him for a fee at Will Call, which might be the solution here.
No, it's not. If you are physically incapable of operating a piece of technology, the ADA covers reasonable accommodations for that. If you are simply unwilling to learn how to use a piece of technology, it doesn't and shouldn't cover that.
Being a luddite is not a protected class.
The OP video actually addressed this: He went to the physical box office, and they seem to be able to print individual tickets. Just not a season ticket, for some reason.