I think the main issue that would have to be addressed is the "turn cash into bitcoin" step.

While I havent personally done an in person bitcoin exchange, I'd imagine that there aren't too many people doing it this way, and probably not in quantities of $1000+. I would love to hear about the experiences of people who have done this.

The other option would be to setup a bank account, which might be a bit of a challenge if the person is not a citizen, or perhaps not even in the country legally, and then there's the issue of the money now having a permanent digital paper trail (not bad per-se, but probably something your typical migrant worker sending money home might try to avoid (but seriously pay your taxes))