Ok, I will give my input. But it's from a theoretical viewpoint. I do not think anyone should break the law or do anything illegal..
I've been asking myself this question for a while now. We have to remember that Bitcoin is no longer an experimental payment method - it is now a competing currency and is now recognized to be a viable threat to the existing financial system.
I have no doubt that Bitcoin users are now under increased scrutiny by the government for many reasons - including to try and discredit them in order to hurt Bitcoin's image. Take a look at Charlie Shrem as an example.
How does a tinfoil-hat-wielding Bitcoin user cash out truely anonymously? I know that cashing out anonymously has been discussed many times before but there are problems with all of the methods I have seen.
What we want to do is convert to cash, just to be clear.
Face-to-face cash
The main problem is of course that the other party knows who you are (what you look like, phone number etc).
I was going to do a f2f trade with someone before, prior to the trade I background checked his username and the guy had posted online that he buys from Silk Road and hinted that he sold drugs. So when you meet someone they could very well be an amateur drug dealer. This is obviously very bad for many reasons, they could be under surveillance. What will the police think when they see a dealer handing you lots of cash?
I've refrained from doing f2f transactions because I do not like the thought of meeting a stranger. Where are the best places to meet? How do these usually go down? has anyone had any bad experiences?
Always meet in a public spot, and do some checks on the person you want to trade with in advance. You could use a third person to actually pick up the cash, for instance some teenager or whatever that wants to make a quick buck without asking questions. Communication with this third party could be done over a cell phone that you've bought anonymously, and could be discared afterwards, so you did not release the bitcoins until the 3rd party had the cash in hand. If you rusted the trader, you could send the bitcoins in advance as well (but that would be more risky - but you wouldn't have to buy/get a cell phone for the particular case). If using a cell phone, or a pay phone, use it from somewhere that's not near where you live, perhaps even in another city. You could also in its entirery conduct the trade in another city than your own. Then there's the question of delivery of the cash from the third party to yourself. To protect yourself from losses, you could exchange in several trades instead of one large one, so if the exchanger or the pickup dude cheats you, you do not lose that much.
The swap of the cash could be done 'spy-style' in a crowded toilet where you simply swap a similar looking suitcase/bag/map by pushing it under the wall to the nextdoor stall, where you pick it up, or the envelope with cash could just be pushed under the wall in the same style, and the 3rd party would leave the toilet with any followers not being any wiser. I'm sure you've seen many movies and could think of endless ways of doing this.
The main point being that the 3rd party should be able to deliver the cash directly to you, some associate of yours (which would lead to having to trust even more parties), or being left at some pickup point for you or someone else to pick up later.
To avoid possible tracking by an agent, use a faraday cage (can these be had as a purse or similar?), or use a radio signal jamming device. That way there would be no tracking device along side the cash that could give signal to the outside, and once in your posession you would check the cash, and crush any transmitting device if present, before it could provide any signal to the outside world.
I provided some information about this before, in this thread:
https://bitcointalk.org/index.php?topic=455824.0Suggesting that a drone could be used to pick up the cash.
When exchanging cash, to avoid any followers, use moving objects (bus, underground), and drop the envelope somewhere 'safe' that only you and the pickup boy would know about.
Using a human as a proxy to get the cash is always risky, as you need to trust that person, and that person needs to accept the risks he's taking with the operation, or he's so stupid he does not see the risk, and then it could be difficult trusting him.
As for person-to-person exchange between yourself and that person, a crowded public toilet, an elevator, a train, bus, subway or whatever could be a good idea. The point is to make the exchange without anyone noticing it happens at all - and by doing it somewhere where it is hard to follow you makes it safer.
Your level of paranoia determines how much precations you should take. It could also be wise to not have the 3rd party knowing your ID at all, so even if he gets caught, he will be unable to say anything about you, even if he is pressured.
I really do like the drone version though, it's quite high tech, and will demand a lot of preparations, but it would be hard to track. You could have a camera on it, or even a supporting observing drone that films everything to ensure nothing nefarious happens, and the pickup drone could have a small faraday cage where the money needs to be inserted. So the exchanger puts the money into the small faraday cage on the drone, and you send the coins to the exchanger, or there could even be a set of private keys delivered by the drone, the possibilities are endless, the only limitations are your imagination, and your level of expertise and how much money and time you want to put into it.
As for following the drone, I don't know how feasible that is. At the present I guess the number of drones is pretty low, so there's a very slim chance your drone will be followed, and the more twists and turns and distance it does, the smaller the chance it will be followed. To make things even more complicated, it could even drop the cash on a moving object, for instance fly under a bridge on a highway, and drop the entire faraday cage on the back of the truck, then getting out of the bridge at the other side as if nothing happened. I'm sure it could be constructed so that you could not visibly tell whether the cash has been dropped or not from a distance. The drone could then be completely discared for every transaction (you'd need to be very rich to do that..)
I'm looking forward to the first Hollywood movie where they do something like that!
Cash in the mail
Same problem as with f2f, the other party has your address and knows who you are. You could use a P.O. Box but you still need ID to open one. The other thing is its possible the cash is stolen in transit or intercepted. You are going to come under increased scrutiny if post office/customs see you are getting cash in the mail every week.
Solution - set up a mailbox somewhere random, perhaps somewhere where it is so crowded already that nobody will notice. Preferably somewhere where things are a bit confusing, for instance where students live, or similar where people move in and out regularily. Nobody would notice if there came a new name on one of the postboxes. But you needed to somehow have access to that mailbox. I'm sure you could think of various ways to get a key, or if the mailboxes are separate, you could even get a similar one, and set it up with a new name tag on it. You would not use your own name for sure, and you would also want to make sure that nobody else used that mailbox, and that it did not look suspicious, if there was 5 neighbours somewhere, and some Mr.Anderson moved in, they would be pretty curious as to why that is, and the mailman would most likely notice as well. And when doing this, you should not use the same location for a long time, and just request small amounts of money every time. Remember that the US postal system takes pictures of EVERY package ever delivered (from what I've read), if they inspect and monitor for cash as well, I don't know - but some kind of wrapping of the cash so that it cannot be easily detected could be a good idea. You could also set up some covert surveilance where your mailbox is, so you could notice any suspicious behaviour, and if that was the case, just abandon the site altogheter.
In short - don't be greedy - don't be at the same spot for too long - make it confusing. You could also instruct any exchanger to write you a letter in addition. For example. "Hi Tom, I want all the best for your college education, I've sent you 700 dollars for your birthday. Regards, uncle Jon."
There's also the possibility of 'Poste restante' where you have a package sent to a post office, and you have to go get it there. But you'd probably have to show some kind of ID..
You could also find an abandoned house and set up a mailbox there, making it look like someone moved in. There would of course be risks to that as well.
Whatever method you chose to use, write down the risks and the benefits, and then see if it's worth giving it a shot.
Western Union
I've never used WU before. What information do I need to give? How does the process work, what do I have to bring with me? Does WU give any guidelines on how they hold the information and under what circumstances they give it out?
I would think they're very concerned about AML/KYC - but you could read on their website their terms, and then you could always try a small transaction and see how it goes, and what kind of information you need to give up. Note that all of those transactions are tracked, and there's most likely video surveliance in their offices.
Anonymous visa
There are a bunch of these anonymous visa cards going around which are issued by banks in Poland. It looks like people are somehow able to open accounts with fake details and they then send you the visa card in the mail. It's supposedly legal. It sounds great but I have heard of customs seizing the cards or even the bank disabling them. Does anyone know what the legality is with these?
Does anyone have any ideas or know how one can cash out truely anonymously? Please share your technique and if I like it I will tip you!
As long as you have a working card, a merchant is probably completely uninterested in where you got it, as long as they get paid. Aquiring the card also has risks, for instance it could be intercepted, confiscated, or the police could be coming to your door, so then having a 'safe' maildrop would be wise. Once in your posession, everywhere where you use the card will leave a track. So if you constantly use it locally, then the taxman will most likely start to become interested. Go to random different places, preferably in other towns and withdraw cash. Use a costume when doing this, cap - fake beard - big jacket - whatever, so that there will be no easy evidence left on the ATM security cams. Also you could be pretending to have really back pain, and complain to some random stranger that you really need to extract some cash from the minibank, but can't even get out of the car because the pain, and see if you can get some help, even offer them a small amount to help out. Try to locate somebody that looks like they're willing to help. An old lady, or something like that. Risk is that they might go off with your card in its entirety.
Also take into account where you're going to conduct the trade. In Miami I would be careful, as there's been a lot of sting operations there. In Finland you'd probably be entirely fine.
Another option could be to buy something with bitcoins off a site, then have it sent to you. Then resell that for cash. Also, as more and more merchants accepts bitcoins, you could actually buy a lot of the stuff and services you desire directly with bitcoin.
And in the end, perhaps the nerve wrecking implications and elaboracy of it is not worth it, and you might be better off paying your taxes and sleeping well at night?
