Sending e-mail via a possibly sanctioned entity

This is an example of a quasi-anoymous communication system that sorta works (except for the glaring problem that it's a literal *phone* which means you're going to be "anonymously" tracked by $telco and/or anyone running an ISMI catcher)

Take away the "phone" part of that and you can piggyback off of public/"open" wifi, again for varying degrees of anonymity. That said, a not-terribly-repressive regime can easily require folks to require some sort of government ID and/or tied to your device [1] as a condition to grant access to said wifi. And said regime can easily require all traffic to be routed through "great firewalls" or some other classification/inspection/tracking system [2]

And sure, you can interpose middlemen, but when $oppressive_regime has no qualms about disappearing its own citizens, all you'll accomplish is a slight delay in how long it takes your door to be kicked in.

> One option is for me to use Tor to go to an anonymous online bazaar. Then to use an anonymous distributed payment method

Again, the vulnerability here is the ability to convert this "payment method" into $national_currency on either end. Those exchanges are the choke points that governments can, and do, go after.

...I keep coming back to the "what threat vector are you trying to protect yourself against" question. Because a guido wielding a gympie trounces technical handwavery... every. single. time. (see xkcd #538)

[1] I experienced this a decade ago when traveling in the Middle East.
[2] This capability continues to be demonstrated by China