As we saw the other day, Michael can, in fact, accurately judge what the result of an action will be if he has a good idea of who's doing it and why. He's no Liz to assume that people will be his friend because he's got good intentions and thus has a fairly good idea of why Thérèse and Liz don't get along. The reason that he's as inept at leading his own life as she is comes not from his not having an idea of what the consequences of his actions will be. The reason is that he has very little idea of who the people around him really are. From what I've seen, he divides the world into three categories: potential allies, heartless authority figures who want him to writhe in the dirt as they laugh at him for making mistakes and heartless liars who trick him into exposing himself.
I'll get to the damage that the first category of people cause at the end of this essay but I'd like to start with his war against people with no sense of human. It seems to me that his unresolved and unresolvable issues with his domineering parents have made him see authority figures as a menace to his dignity. The best example I can think of is Evil, Ambitious Mira who thinks that nothing he does is ever good enough. Since he can't wrap his head around the idea of someone who wants to tell him what do to genuinely doing so for his own good, he's doomed to struggle against her generosity for years to come.
We also have to remember that his dread of being humiliated has made a raging paranoiac of him. The best instance of that is his witless over-reaction to the direct consequences of Martha's friends telling her "If you keep what Mike told you a secret, you'll be an outcast with no protection from anyone"; since the poor deluded clown can't see that some promises can't be kept, he squeals about lying liars who trick him. (This explains why he's on Team Anthony, by the way; he's primed to believe that sneaky women want to trick honest men.)
The nasty side-effect of all of this is that people like Deanne who promise him salvation from tyrants and liars can play him like a damned Atari. Most of her career has been spent approving of all of the stupid things he does so she can make of him the perfect excuse for her own refusal to thrive. It's sort of like he's a male version of Elly; she's got dark hair and she's a malleable paranoiac too.