I've had this idea many times. I actually bought my bitcoins in person with cash. I'll tell you what the experience is like:
First I waited at a subway station. He was 10 mins late, so I was constantly looking around for him, looking fairly suspicious. Once he arrived, I immediately knew it was him. Ever seen a hard core crypto anarchist in real life? Yeah, long hair, dark clothes, amazingly friendly, super intelligent, totally has a file over at Mosad, CIA, CSIS, etc.
Did the cash exchange, but it was awkward. Do I give him the cash first? What if he runs away? Same with the transaction. Oh and my block chain was out of date and updating it on Starbuck wifi took forever.
In the end it worked out and we went for beers afterwards. He was a really interesting guy. I think the main problem is that either side could rob/rip off the other side. But I think it could work, and it is one of the few way to stay anonymous.
The other way is to get a lawyer friend of yours to walk into a bank and send a wire to a Ukrainian bank account. That way even if they look at the security tapes you are covered.
