No it was an inflamitory insult 98% of the time
For like the last four to eight years its just been conservatives are racist
Conservatives hate the poor
Conservatives are bigots who hate gays blah blah blah
Depends on where you look, tbh. It's not like there hasn't been hella' outreach to traditionally conservative groups. It's been constant for years; said it earlier, democrat outreach and programs are about the only thing actually trying to help a lot of them. The conservative media in particular haven't been reporting on that, obviously enough, but about the only groups that haven't been getting attention from democrat efforts are, y'know, the actual bigots, people actually trying to further ruin the poor, and so on. Which they can't really do much about. There's no common ground, and they're not going to listen over the course of a few years. Few decades, maybe, but that's kinda' been happening.
Bigger thing as it goes is that the actual bigots, people trying to ruin the poor, and so on, have been getting increasing influence and control of conservative media and political apparatus. Makes the whole process significantly more difficult. Hard to talk to conservatives when they're letting the folks they are be their gatekeepers and representatives.
As for the money thing. It's been noted repeatedly he's almost certainly been underperforming simple safe investment -- the same sort of thing he's insulted and claimed he was better than. Good chunk of actually competent businessfolk have commented on his business acuity, and it's rarely been flattering. That he's done as well as he has (which, again, is probably worse than if he had done nothing but invested the money and chilled) in
spite of his business competence. It's been other people pulling his ass out the fires he got himself in, with a side of people actually trusting him and the expected happening.