Good for your friend! Only thing that you can really do is be there for him and encourage him - he's the boss of this but good luck to him.

Only thing that ever worked for me was vaping. Patches, gum and everything I'd use to wean off but I'd start smoking again very soon after. Going cold turkey never worked for longer than a week.

I think the first vape I had was 2012 and I've used one since. Genuinely changed my life. I don't really have plans to quit vaping.