Wealthier people are by far the most difficult customers. They think they're entitled to everything because they're "rich" and "above" wage slaves, so they get pissy and aggressive the moment something doesn't go their way (and sometimes they'll just make a ruckus for fun). Source: I worked in a few fast food restaurants in the south before
It was crazy for me working at a mexican restaurant and the only people who got argumentative over the $13 for a burrito with just 4 oz of meat (total rip-off) were the ones who could definitely afford it, while the poorer people just accepted it. And the wealthy people always came in again (usually regulars) and expected it to be more every time.
Obama is by far the best president we've had in the past few decades, but overall he still sucks pretty badly. He was the first presidential candidate who got more than a billion dollars in donations for the race, at a time where Democrats were guaranteed to win no matter who they picked because of Bush. He's still "the establishment" that American voters hate so dearly.
Democrats should run a candidate more like FDR (who won FOUR terms as president) or Harry Truman or Jimmy Carter. A social democrat, an actual leftist-adjacent candidate. I would say someone like Bernie Sanders, but that ship has already sailed long ago... Socialist policies are popular with average Americans when nobody tells them they're socialist.
Unfortunately, the Democratic party leaders are owned by corporate money so that's not going to happen. We're gonna keep getting stupid shit like Kamala's "tough on crime" and "locking down the border" rhetoric, instead of "universal healthcare" and "zero-tuition education".