That makes it far less likely that he's a plant. Why would he damage he continually damage his bottom line to get Clinton the presdiency. What's in it for him?
I've seen many political analysts speculate that Trump is setting things up to start his own Trump TV network after the election. By pandering to the alt-right and questioning the validity of the election, he is the pied piper leading the far right of the Republican party and independents to his platform.
So yeah, he's damaging his traditional Trump brand, but he's been doing that since the primaries. But he may be trying to reinvent himself as the leader of a Fox News replacement. I don't think he is doing all this just to destroy his wealth and image. I think he's trying to create a win-win situation.