I do this exact thing. I want to see hexbear grow and will sometimes upvote a baby leftist with a bad take if they indicate a willingness to learn. Just like you said, I want to encourage them, and signal with a little hint that even if they're getting rightly excoriated for something, that their willingness to stick around and talk about it (without the typical liberal bad faith bullshit) and learn will be rewarded here. I realize it would be best for me to comment and express this exactly, but for one it's not always appropriate to do so given the context, and for another it's simply not always practical for me to type out a reply, depending on where I'm at and what I'm doing while browsing the site. I want these baby leftists who are steeped in inescapable propaganda to stick around and get dewormed, (rather than get turned off by a dog pile, even if it was justified, and go do the easier thing of hanging out on fucking .world where their brainworms will only multiply). I want this for their sake and for the sake of the site via community growth.
But now I feel like I could be punished for that, or even if not punished, that some mods will be looking at my upbears and thinking to themselves that I'm a shitty person. That I harbor reactionary beliefs that I don't actually believe because I upbeared a comment that contained a reactionary sentiment. Maybe that shouldn't matter to me, but it does. I'm extremely sensitive to that sort of disapproval. It's already why I don't comment a lot more to be honest. I can't not think about it, be effected by it, and it simply makes me not want to upbear which also sucks because that's mostly how I engage here.
There are also many times when I read a comment and I'm enthusiastically nodding along for 90% of it, but then run into something I strongly disagree with. But because the rest of it was good, I'll still give it an upbear especially if the user seems to be speaking in good faith (which I may or may not have accurately judged!) Once again, ideally I would respond and call out that one thing I disagreed with, but like I said, it's just not practical for me to respond most of the time. Now I'm going to have an internal debate every time that happens about whether I should upbear it or not, who will think ill of me if I do, and that will inevitably make me feel shitty and worry, even if needlessly so, and in turn, I will feel turned off to wanting to engage with the site.
Maybe I'm just too neurotic about this sort of thing and that's on no one but me. But I can't help it. This little episode has had (or will have) a profound chilling effect on how much I want to upbear which in turn has a chilling effect on how much I want to engage at all.
You're not missing anything. I shouldn't have included the pic but I had just seen it minutes before reading the post and it felt like it fit. The one simple trick is what you said: eating the rich.