I'm not sure I see him as a rebel leader/dictator/civil war type. At his core, he is a coward who constantly makes mistakes. He is an isolationist loner who thinks everyone else is either out to get him or incapable of their jobs.
Many dictator types are like this. He may not have a plan, as such, but his actions could easily lead him a path of undermining democratic checks to the point of becoming a dictator.
He has business nous, but it hasn't quite translated to political might.
Yes, I'm not sure about that either. He seems very much a one trick pony. He develops real estate, which he learnt from his dad. His other ventures have mostly flopped and his casino ventures led to bigly bankruptcies at a time when other casinos were doing very well.
He's borrowed heavily to build his real estate and golf course empire, and he's not disclosed how much he owes.
He's been a survivor so far, though. I hope for his sake that this Presidency won't be his undoing.
He could become a Bernie Madoff just out of sheer stupidity and hardheadedness.