His Wall idea only appeals to building companies and morons. Proven method of slowing down migration is to remove the benefits of migrating.
Obama care. Taking that apart will hit his voters, they're the people who need healthcare they can afford. The reason you're ass raped over medical care is the insurance companies and costs.
Stopping imports from the Third World. Should he even stop the rise in imports, again it's his voters who will be hit the hardest. The price of goods in US shops will rise. Should he manage to start getting jobs back to the US, prices will climb fast.
Spending on the military he won't use.

Where's the money coming from?
Cutting taxes = cutting jobs and people going on benefits. Cheaper but devastating to places those government employees rely on to shop and spend money. Could be your customers.
Everyone knows Clinton is no Saint. But a crooked man telling a crooked story about a crooked girl. Doesn't hide the facts. He wants to lose the election because he knows he's in over his head. This was an ego trip that went horribly wrong for him.
As for his successes. Being successful doesn't mean someone can step out of my comfort zone and up to 10 levels.
Can a market stall owner run Macy's?