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>Wouldn't it be obvious from following that who is ultimately benefiting from this?

It would not, unless you could trace that address to a person.

There are coin tumbler services that supposedly "clean" the origin of whatever crypto you are using by exchanging it.

There's also Monero, which essentially has this feature baked in.

Cashing out anonymously can be difficult- localbitcoins allows you to basically conduct ad hoc exchanges of crypto with other people.

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