I would say his comfort level is with old school, so your job is to introduce him to new technology.

Bring a couple of Sonos One speakers out, and leave them with him for a week so he can play. Show him how the installation will be magnitudes cheaper than what he has in mind.

If he has his music on a desktop computer in iTunes, then you can set it up as a share volume on Sonos, and show him how quickly he can get to all of his music without walking to the main room of the house.

Usually Sonos sells itself.

I will sometimes set it up and leave it for people like that, other times I show them screenshots that I have saved in my phone or tablet to give them a vision of how well it works.