assuming trump has no earlier DJT grift, and the stock stays elevated (~late Sept) after insiders clear sales restrictions : is it possible that this would sways trump's opinion on a money losing company with negligible subscribers and revenue?

This theory of the stock presumes that the company won't be losing money, and won't have "negligible" revenue, if Trump wins the election. That if he wins, you'll see a massive uptick in companies and other folks putting ad buys on Truth Social.

Might he sell out of DJT in September, when the lock-up ends, and take his chips off the table before the election? It's possible....but remember, he'd take a huge haircut from the then-current stock price. You can't just dump 60% of the shares of a company (and whatever multiple of the daily float that would be) on the open market and not expect the price to crater. And that goes double for DJT and DJT, because the company only really has value to the extent that Trump is perceived to be invested in it.

So unless he's cratered in the polls, he'll probably bet on himself winning the election and being able to more slowly divest himself of a portion of his ownership over time, so as to not crater the share price.