If he really wants to watch Phantom Menace first, I suppose it would work if you jump from it to A New Hope.

If he is truly ignorant of Vader being Anakin, he’ll see a movie with kid Anakin, followed by a movie with old Obi-Wan lamenting how Vader killed Anakin at some point in the prequels, leaving the big reveal in place. Maybe actually making it better in some ways.

Honestly I don’t think Rogue One is worth watching. It’s pretty, but was very meddled with. I would highly recommend perhaps putting the Andor show in place instead of it. Either way, watching these after Episode 1 makes sense to me.

Then do the normal Machete Order.

If he doesn’t remember that the Han Solo movie exists, don’t remind him.

Of course that’s a BIG commitment. The sane way is to convince him just to watch the original trilogy first and the rest if he likes it.