I think it's likely just normal, everyday arrogance and incompetence endemic to the tech bro culture. Musk is outsourcing these efforts. I guarantee the winning presentations included the terms "disruptors", "data-driven", and "six sigma." The superPAC has previously fired In Field Strategies in Florida (Rolling Stone) and the September Group in Nevada/Arizona (The Guardian)". Not surprisingly, Musk's SuperPAC is poorly run and surrounds itself with poorly run vendors. It gives me some solace that the world's richest man throwing money at Trump's campaign is about as effective as throwing it at a literal dumpster fire. They don't understand regular people, which makes it impossible to manage canvassing, which is just regular people talking to regular people.
Now compare Musk's / Trump's campaign against Harris's. It is supercharged by young people, who have known Trump since before high school. They are clever, undaunted, and fully committed. This isn't just about a paycheck for them. I have high hopes for this generation.