Not that I have much experience onboarding but I would actually send them through the primal route. Easy onboarding and a quick wallet setup. Then they can get more technical as they go from there and move to other wallets and freedom tech and go as deep as they like.

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I'm halfway debating trying to push him in the route of a Shopify site with a BTC pay server. That way he can accept both Bitcoin and fiat, but also advertise on Nostr

Sounds solid.

Another route would be setting him up with phoenix wallet set up a lightning channel and you can help him by hosting phoenixd and set that up with btc pay

Yeah, I'm probably going to have to act as an Uncle Jim in some fashion and let him use one of my existing lightning nodes.

We need more Uncle Jims

I do it for as many people as im comfrotable doing it for.

t-y Uncle Enki!

Might also want to checkout Zaprite

this is what I was gonna suggest. lots of options on how he can cash out as well. Shopify is a little more expensive, but it has a lot of functionality for someone just wanting to sell stuff and maybe get some Bitcoin for it.