I think you should actually talk to him. Do avoid calling him out, but ask him a few questions. From my experience, right-winger usually recognize that there are things that are fundamentally wrong in society. They often get to an inch of attaining class consciousness before concluding “It’s the minorities’ fault” or something like that. If he doesn’t already believe that, it shouldn’t be hard to convince him that capitalists are bad (if not capitalism as a whole). Try to focus on the filthy rich ones first, lest he become defensive. Avoid focusing on the individual characteristics of capitalists, and more on their behavior as members of a class.
If you’ve done some reading, it shouldn’t be hard to find more plausible reasons for society’s ills than the ones he was taught. Just take it slow, seed some doubt in him and let it grow on its own. If you give him a good basis, he might very well reach a close to communist conclusion on his own, which will implant those ideas much more firmly than if they’d been fed by an outsider.
However if he’s the billionaire larping kind, I’m afraid there’s nothing I can say to help you.
Happy to know my input helped, and happy for you for having done something good.
As for the new issues that arose, I may have a few ideas.
When it comes to Trump, I don’t think trying to change your neighbor’s mind about Trump would be productive. Instead you can dodge the issue by trying to convince him that who the president is doesn’t matter, that the power structure of a country can never be summarized to a single individual. If he’s a fan of the “deep state” theory, then could be easily convinced of this. Like last time, avoid focusing on individuals, but rather their collective behavior. For example, a capitalist is forced to follow the rules of capitalism, lest they get out-competed and/or lose their class position. Cops, officers, judges, etc fonction similarly.
As for immigrants, you could try the “let’s stop invading, couping and sanctioning third world countries” approach. If those countries were allowed to develop independently, without IMF restructuring, civil wars, and while being able to control their natural resources, immigration would basically be a non-issue (beside environment-related ones).
One last thing, maybe discussing about planned economy could be useful. You can start with things like the military-industrial complex, which he would likely agree is a massive waste of ressources and by extension lives. That approach should be particularly effective if he’s a veteran, but even a “patriotic” Trump supporter could be swayed by this. After that you can extend your reasoning to heavy industry, transport infrastructure, etc… You can try invoking China as a competitive comparison if you think that would work. Similarly for healthcare, only mention it now if he’s likely to respond positively to it.
I’m not really proficient when it comes to LGBTQ issues, so I’m afraid I can’t help you with that.