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The Trump-loving libertarians are a weird batch. Typically the trumpanzees I deal with are GOP, and my strategy is to actually talk up the LP in an attempt to use Chase Oliver as more benign trash can to drop would-be Trump votes into.
For actual libertarians who are already planning on voting Oliver, I point out that a fascist victory would be fatally damaging to every party except the fascists - 3rds are fucked right along with everyone else. Their best strategy is to nudge the current system into a model more conducive to a 3rd party victory, specifically via ranked choice voting so people can feel safe voting for a 3rd without worrying about the spoiler effect. To do that, they need to vote blue to keep the fascists out of power, as a vote for more time to refine their party of preference and preserve a political model that could lead to that party's victory.
Trump LPers are harder to speak to, to the point of being a lost cause in most cases, but I can understand wanting to give a little extra to help out a family member. Start digging into policy questions - less who he wants to win, and more what he wants to accomplish. Assess those goals, and consider if someone other than Trump would be better to achieve them.
This debate technique is called "steelmanning" and requires putting yourself in the other side's shoes, and building their side up in a way that's compatible with yours, vs the usual talking points nowadays, which are usually just strawman bullshit that will never get anything done.
Good luck!
Good ideas! I'll keep some of those in mind. He's not stupid, just incredibly naive, and it doesn't help that he lives in the big shadow of his special forces older brother and thinks (maybe subconsciously) he has to prove himself equal.
Because of his naivete, he listens to what the right wing news orgs say as gospel, possibly because he has a weak epistemic foundation. If I can manage to push through some of that bullshit, it might give him some space to form his own opinions.
I don't really want to change him, per se, but it worries me that he's so thoughtless; if I can help him learn how to put a little more thought into his choices and actions and see that life doesn't exist in black and white terms, I'll call that a success.