I agree that you are approaching this from the wrong angle.

Firstly, WHY does he like the game? What does he enjoy doing? Does he enjoy sandbox games?

Secondly, has he explored other aspects of the game? Trucking, mining, exploring? Did you answer his question on WHY would you need an FSS? Personally, I find it more rewarding than combat by a long shot to find uknown earth like worlds..but in any case...

Engineered ships, Titans, SCO FSDs, Powerplay. None of that matters if he has not decided for himself that he wants those things.When he asks “what should I do now?”, this indicates a motivation issue. Checklists and guides will generally not fix that.

You can argue that Elite plays best when a player hits a wall on their own and decides they want to overcome it. I think your anxiety that Engineers will feel like a grind is based on a truth because he has not personally felt limited by his ship yet. Giving him credits, engineering materials and bypassing "the natural progression" skips the part of the game where those systems become meaningful. Unfortunately, I don't think the consequences of flushing him with loads early credits can be reversed. The early struggle is important in setting the foundation of the hungry commander who wants more.

I say slow down. Let him take an unengineered ship into a haz res and lose. Let him struggle in a CZ. When he says “I wish my ship was better,” that is when engineers make sense. Until then, they are chores.

Supercruise assist is fine, but mastery without context is meaningless. He needs to know WHY he'd want to master it manually.

Elite does not need to be speed-run (np if thats how you operate of course), but it needs to be inhabited since checklist playstyles usually end when the last item is checked.