I don't think he cares about triggering the libs or dog-whistling to 4chan incels. None of that affects his bottom-line. It's pretty obvious what he's doing. You didn't see him post about this stuff before his industries were shut down.
The way I see it, he's putting on pressure on politicians to relieve the lock-downs and rallying support for his cause among the people most likely to support that cause. The way he's doing it, is a way that he believes will resonate with a modern internet audience, through popular memes and narratives.
The moment that the lock-down ends, he'll probably abandon this shtick and go back to making billions of dollars.
If America were like the rest of the world, where "liberals" represent the pro-business side which want businesses to open up, then he'd probably be supporting "liberal" agendas. But America is the bizarro world where things like liberalism take a different meaning. It's much less about any consistent ideology or principles, and much more about timing (who's in charge and when).