Remember NLS
There are two types of law...
The Law you can read, and the one the government chooses to apply to you...
Your Lawyer friends may be right, but so were joe stack's and he got prosecuted...
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.
Money exchanges are required to be licensed and undergo a huge ordeal of regulations and licensing and bookwork in it's operation. If you fail to do this, it is running illegally then. I see e-gold was mentioned here. One of the best examples but not the only example of how the government doesnt like competition or any large assets it cant control or put a hand in. Especially if they feel the service is allowing criminal activities to be hidden.
And I love how someone always seems to bring race into a debate about an unrelated topic. Epic.
Lawyers interpret the vague laws as they believe, the government interprets law any way it damn pleases even if it means bending it or using it out of context. Even hinting at illegal activities, is enough to be taken down which has already been done on his exchange site. It will lead to conspiracy or worse charges.
If bitcoin or the exchange never gets big, the law might not bother with his exchange but if any popularity ensues and especially if taxes arent being paid. It will be taken down by LEO.
The danger isnt in buying or selling bitcoins. The danger lies in a centralized and concrete exchange. Centralization has been the key factor in the fall of many systems especially alternative ones.