Regarding conservatism: it is not like 'conservative' Supreme Court appointees have done a whole lot of good on issues conservatives care about. We have gay marriage and retain Obama Care. Conservatives appear to have trouble defunding Planned Parenthood even after Gosnell and the baby-parts-express revelations. With Trump we might win on the wall and be no worse off on other things.
5) He May Be Reluctant To Spend Money:
Actually this could be a problem. It is not clear how much of wealth is liquid. If much of his wealth is actually embodied in buildings and the abstract concept of 'brand' he may have much less than a ¡Jeb! size budget. He may be relying on bluff-and-bluster and a lot of free air time. So far that seems to working but there will likely be a time when he needs to spend decent sums of money, on ads and ground-game. If that happens will he decide golf and helicopters are more fun than presidential runs?
He claimed he makes 400 million per year. That should be sufficient liquidity.