Trump is many steps ahead of you there. He knows that even when Obama leaves office, there will be a huge machine left behind that he will have to fight or to rout out of the Civil Service, so he is hedging his opinion so as not to set them against a new government completely. Secondly, if he comes out too b & W on whether O is criminal, he paints himself into a corner until he can get his DOJ up and running. People would be baying for a criminal prosecution just to try to make him move dangerously before a full investigation.
Every president gets a major shock when he actually gets privy to the intelligence documents once he is elected. It's not wise to put oneself into a corner with promises that would have to involve rooting out the treachery in FBI, State Dept, CIA and the banking system.
It’s not really that complicated. And I seriously doubt Trump’s thinking goes anything like all you speculated.
But, I am willing to think about it some more.
Trump’s mantra is that we just need smarter people.