How encouraging...you've just told the poor fellow that even if he does everything right he could still go to jail--you're making him feel like an ethnic minority!

In most cases though, if a lawyer tells you you won't go to jail, you probably will not go to jail.  Newlibertstandard uses paypal, which already practices know-your-customer and he is operating in amounts less than $10,000 which is what the money laundering and tax cheat police sniff out for.  This means he is unlikely to be doing anything that is wrong OR anything that will attract the attention of Law Enforcement.

However---

Thinking ahead to bitcoin's future--money changing services that operate on a large scale and don't practice know-your customer would indeed be illegal and would thus have to operate within the onionverse, changing bitcoin to money services other than paypal (perhaps offshore based like pecunix).

Another idea would be for some future crypto-preneur to set up a Mom and Pop shop called "Grandpa Joe's envelopes stuffed with cash" and only accept bitcoin as payment.  lol.