Thanks for sharing that anecdote about your Dad. Clearly there are a lot of people who are willing to think that the CEO v. CEO face-off could be the winning formula for the Democrats. I figured I'd give my 2 cents on Bloomberg, since he was my mayor. We had a love/hate relationship with him, here in NYC. (As an aside, Trump was not well-loved here at all, and has basically always been considered a self-aggrandizing huckster, and worse.) Bloomberg did some good things for the city...he helped eliminate the deficit, he worked on education issues, championed many socially liberal causes. However, he has the same arrogance as Trump in that he ran the city like a CEO, and if he saw something that he thought wasn't working, he just eliminated it, like recycling. He thought it didn't pay for itself. It took a billionaire from another state to get it reinstated. He had the law changed so he could run for a 3rd term, which is worrying, looking forward. (Something Trump threatens to do as to his Presidency.) He favored developers over small businesses and has therefore forever changed the face of Manhattan. We've lost so many Mom-and-Pop's and other things that gave our city the character that made it what it was, and has put in threat those who live here who aren't rich. We will never get back the Manhattan that he helped destroy.
That said, I'd have Bloomberg over Trump in a heartbeat. It's not what I want. I'd prefer an actual policy politician who could lead us back to a more normal system of government, with respect to the system of checks and balances. Someone with real experience at high levels of government, not just business. Someone with a moment's faith in and idealism towards the Great American Experiment, not just some notion that it's a business to be run. But if we get Bloomberg, at least he's an intelligent and reasonable human being, with the capacity to work towards the greater good, as he understands it, not simply as it serves his ego. And he has a big ego. It's just much sturdier than Trump's. He doesn't need to destroy other people to buff himself up.
Trump has already managed to put out audio on Bloomberg saying something racist. He always accuses people of what he's already been accused of, himself. It's going to be 1972 and the dirty tricks all over again. He's gone after Biden, now Bloomberg. He's already tried his best to denigrate Warren. And he's asked NH voters to cross party and vote for the least viable candidate. (Undeclared voters can decide on the day which ballot to take, in NH.) Trump doesn't care about good democracy...he only cares about winning. He makes a shameful mockery of our election process, as Nixon did.