Reddit gold is an example of how to nail something like this, because it was done with tremendous sensitivity to the culture of the site. It's quirky, slightly ironic, riffs on the obvious silliness of a 'gift' that goes 99% to Reddit's coffers, and it's perfectly pitched to the user at the point where they are already feeling the value of Reddit's product & the other user's content. Twitter's, by contrast, is an example of how not to do it, for the converse of all those reasons and more besides.
Putting both together could be incredibly lucrative but also would be treated very cautiously because of potential deplatforming.
Musk actual commitment to minimal moderation (what my mental model is for his free speech bent) could thread that needle and at the very least be a fascinating experiment to watch from the sidelines.