I know that as leftists, participating in online communities requires a certain level of discretion. I’m admittedly not as privacy focused as I probably should be, but I would like to at least minimize the chances of being put on someone’s list. Do I need a VPN every time I open this site or do I just need to be careful of what I post?
It depends where you live. Some countries have stricter censorship than others. Unless you are making some extreme calls to actions or what might be construed as a threat you should be fine.