[silur]

Firstly I hope @Ender you don't mind "stealing" your tag, I'm just 10000% paranoid too

Secondly a bit about my expertise in the area to convince you, you can believe me:
I'm reviewing the code of all software I use, this includes cryptocurrencies (I HATE BOOST LIB AND C++ SO MUCH T_T) . I don't trust anyone
I'm an acknowledged expert in cryptocurrencies, I have talks in financial meetups, keep contact with developers and have some contributions for them too (although many of them are rejected because they call it "too paranoid")

So how do you handle payments for shady stuff and to avoid tracking.

The golden rule is the following abstraction:
With more real-world fungibility comes less anonymity

This means the wider the set of people who are using the same currency, the wider set of people who will be looking for you.
For example the two ends of this stick is paypal and barter.
Paypal is supa-dupa fungible cuz instant mobile payments and stuff, but can track you in no time
Barter is a currency used only by the participants so the law of large numbers with malicious people will be negligible here

Candidates used in the black market currently:

Cash:
Always check for the sequential order of the numbers and check for any ergodicity (system)

Police and tricky people are smart, if you check only for the incremental vaules you can still be busted, always check for modulo equivalence classes
and markov-chains!
My method is to quickly cash the cash (haha) in different local small groceries that has no cameras and stuff.
If you watch out for these you are 90% safe, money that has only material fingerprint can be washed easier with material methods

Bitcoin
BOOO

Just don't. It already falls withing the script-kiddie category.
If you know a little economics you know that mathematically and socially there is no currency that is fungible and anonymous at the same time (think of our abstraction). Bitcoin is the currency that prefers the fungibility, much much more people are using it, it's more transparent and more suited to
everyday (non-shady) stuff like cash.
Blockchain analysis is a real threat, the math behind it is strong and has great success believe me. Bitcoin's blockchain is one of the most transparent ones, govs and feds can track you even if you use the good old "new address for every transaction" trick.

Let's head to the anonymous currencies that can be found on many deepweb stores!

Dash
While the philosophy of a decentralized open-government is okay, they take too much attention for the marketing than for the actual product itself. A typical mistake. They publish posts about "look we are much better than XY currency use us" and their proof-of-work algorithm (which was originally utilized by the predecessor of dash) is full of bullshit. Firstly it's hard to find like they don't want you to know it, and when you find you will shit bricks of laughter because it's just a chain of already deprecated proof of works. No kidding they are just put 11 already known algorithms  in a bucket and call it a "revolutionary new anonymous protocol". Nope

Zcash
I was really excited for Zcash and I was following them from the start, I was active with them on IRC and I was happy when they announced that the protocol itself is ready. They utilize zero-knowlede-proofs (MATHS YEAAH), it's well documented and they have GREAT people working on it.
This is the first currency I saw that was maintained by people who really know their stuff. Mathematics professors with PhD-s in zero-knowledge-proofs, Software engineers with PhDs in algorithm optimization everything was like a dream.........
But then the govenment attacked. They were greedy, and registered the whole thing under a company registered IN THE US.
They implemented a feature that PREFERS INVESTORS FOR MINING. No kidding if you pay for them, your mining reward will be much more.
I don't have to say that china and the US government instantly invested a shitload of money in the company and already has the majority of the mining rewards.
Zcash went full bitch.

Monero
This is my current choice.
The protocol documentation is good, they separate the theory from practice (they have an isolated repo called Monero lab) and don't fear to make a soft-fork when something happens.
I'm also active with them on IRC although they seem to don't like me because I had an argument with them about the math behind their ring-signature anonymization, I thing It can be increased from 10 ring nodes to like.... 10000000.
But the overall protocol is well-thought, you don't send money to an address, only for a public key that is derived from an address and when the blockchain wants to determine who to send this amount to, you announce this address with your private key but in a way that in a specified "ring" of users, nobody can tell who announced it correctly, only that everything was okay.
The proof-of-work "cryptonight" is well documented and the math is okay, it's also egalitarian, it means that Chinese companies cannot profit more with their 100.000$ miners because the only device that can mine it efficiently is a normal everyday computer.

Final results:


                    Open source | Open government | Good code quality | Math is okay | Prefers anonymity before fungibility
Cash     |           -                 |                 -                 |                -                 |         -               |                                   -                                  |
Bitcoin  |            +                |regulated&tracked|                -                 |          -              |                                   -                                  |
Dash      |           +                |                 +                  |                 +               |          -             |                                   +                                  |
Zcash     |          +                 |               -                   |                  +               |         +              |                                   +                                 |
Monero |            +               |                +                  |                  +               |          +             |                                   +                                 |

[Bish0pQ]

Very usefull information, thank you a lot for this. There were payment methods I didn't even hear off, so I'll definitly check those out.

[FurryRock]

OT: Hell, I didn't even know Monero exist, I might not use it the way you might have in mind, but I'll keep in mind for investing in later on.

[Darkmuseisbae]

This is pretty useful information. Thanks!

[pvnk]

I read every word of that. Not only did you make the information digestible, you offered insight and critical analysis of an inherently concrete foundation. (math)

This remains a resourceful thread that is current and extremely informative. Good. Fkin. Shit.