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At least for the hosting part I guess he didn't search hard enough. Hosts like http://www.mediaon.com/ are accepting even cash via regular mail to start an anonymous website/register a domain.

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https://www.nearlyfreespeech.net/about/mailing seems to allow anonymity as well.

How? Don't checks have your name on them, or doesn't the bank know it?

Cashier's checks and money orders would just have the merchant's name on them, or no name at all. You can purchase either one with cash.

Ah, thank you. That's pretty handy, too bad I'm not in the US.

Looks like they don't (except under very specific circumstances which include not living within the USA)

https://www.nearlyfreespeech.net/about/faq#Anonymous

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