askchapo

I think it's an unforced error to try to relitigate the Soviet Union with people, even if they bring it up, though it seems your friend didn't. I think it's better to be forward facing and the only time you really need to dwell on these sorts of litigations is if you're trying to figure out specific tactics, some historical group had a good solution, and your buddy is like "isn't that what evil people do?" In an interpersonal relationship and not an org, that will rarely come up.

The point of attack should be liberal philosophy, which seems to be a prominent phantasm in this person's mind and is very commonly what people get hung up on, and it's something that cannot be ignored. It's liberal philosophy that underpins all the justifications for the current world order, so if you want him to radically cut against that, it's more productive to argue, say, utilitarianism being the more rational framework compared to bourgeois natural rights that allow people to pretend it's an a priori moral law that they can buy up all the housing and then profit off of desperation.

Lastly, if you see they're in an anarchist direction, support that instead of trying to make them precisely what you are. From your description, it seems the most likely path to success in that department (if they ever move at all) will be from becoming an anarchist first and then learning about other forms of leftism. Or just let them do their thing and be an anarchist, since it's not like it's a divide that is terribly important when we are short a revolution.