I hate to be rude to these people, but you start talking about Actually Existing Socialist Countries and all of sudden you feel like you’re talking to a libertarian who hates prisons. And I’m like have you read any of these… and its like nah.
That’s why I often don’t really suggest Naomi Klein and Bullshit Jobs because they are great points of entryism, but they just give permission for westerners to still have no historical understanding of the world around them. Spouting off about Totalitarianism.
You can glean useful information from books that aren’t explicitly communist too.
If your goal is to convince someone of communism, books by “left” libs written against rightists that are selected partly on the basis that recommending a communist would be scary is hamstringing yourself. The scope of discussion, and especially of positive alternatives, will be very limited and it’s also just kind of dishonest in this context. If the pitch was “I’m a communist but I think this lib academic has useful things to say about some given subject” I would not be objecting because I think that’s true of basically every subject.