When I started using Linux I distro hopped a few times before finding mint, now I have been stuck on mint for a few years, but I still dream of hopping again.
When I was hopping I was in high school, so I had time, now I got to work and hopping takes too much time and effort to set everything up again. If I had a second pc or a laptop I would do it.
If he wants something similar to windows, get Linux mint, it’s the best parts of Debian/Ubuntu but made modern. If you can do it on Ubuntu, you can do it in mint (like online guides cuz mint is based on ubuntu if you couldn’t tell).
I keep dual windows on laptop for rare occasions cuz I don’t like dealing with passthrough for special USB cables that require their own drivers on VMs