I think he is a micro-manager who is tone deaf to politics with no charisma, but he recognizes his own weaknesses as most successful men do.
I think he is going to rely on his pros, ad buys, and proxies to make the case for him.
It will be interesting either way, but the big donors and the DNC (he solves the money problem) appear to be moving towards him. The punditry class, who take their lead from the DNC, will come around if he can start making a good showing in primary races.
I don’t see any way they can keep the Bernie crowd happy and they clearly do not want the Bern. The next best option might just be the guy who will shower them all with cash even if they hold their nose.
[I think he is a micro-manager]