And so we continue...
Sinus pressure is lifting so I can tackle the first question.
I think the viewpoint of conservatives has to do with Elitist behavior and opinions as opposed, to 'brick and mortar' wealth.
Trump has been described as a Blue-Collar Billionaire by his crowd.
To quote Jon Stewart when he responded to Sean Hannity using this term to describe Trump, "that's not a thing". There is nothing about him that says "blue-collar". He wouldn't know how to live the sort of life people like my family lived whatsoever.
Also, as others have noted, "his crowd" calls him that. Yeah. No bias there.
Started with a loan/gift from his father.
Yes, a loan of, what was it, a million dollars? Yep. Totally blue-collar. Every hard-working blue-collar parent totally hands their child a million dollar loan when they're starting out on their own, right?
Had understanding of the building-construction process which eventually evolved into business/real estate development. Respecting his employees, from the guy laying the bricks, to the doorman, to the head architect on his latest project.
There are many anecdotes of him shaking every hand of every employee in a restaurant. If he was in Mar-A-Lago on business and there happened to be Wedding in one of the ballrooms he would make it a point to stop by and meet the bride-groom and shake the parents hands.
This was a question posed in the general section of Reddit last month (not exactly friendly territory for Trumpers, outside of the r/The_Donald subreddit) Interesting read where you get a feel with how Trump interacts with Joe Blow.
People who have met or dealt with Donald Trump in person prior to the race, what was he like?
I have also heard stories of him scamming employees out of pay, families being pushed out of their homes so that one of his multiple towers can be built ('cause he really needs more of those, right?), and then there's also the accusations of him harassing women (and possibly worse) and treating his wives like shit.
If he has shown any positive behavior, it seems to be when he's in public and needs to put on a good show. Which is why it's really funny that his supporters kept claiming one of the reasons he was worth supporting was because he "didn't act like a politician". He's been engaging in that very behavior for years. He's whomever he needs to be in any given situation. You can shake people's hands all you want, it doesn't make you automatically "relatable" to the average Joe.
For a man of considerable wealth, he has done some over-the-top marketing of his brand. Trump "The Game", Trump Steaks, Trump Vodka, buying gold furniture and shit.
None of which are things your average citizen gets to do with their finances.
He was a private citizen. Tends to gloat. However, there are many instances of generosity that he does under the radar. Lends out his plane to get Desert Storm troops home for the Holidays. Transport an ill child that needed special breathing equipment on board.
If that is true, those are indeed good things. But it's hard to square the idea of those acts of generosity coming from the same man who thinks it's okay to judge women based on a scale of 1 to 10, or who's been accused of, again, treating women like shit (and reading his Twitter feed alone should give you a pretty good idea of how he views them). It's hard to reconcile those good acts as coming from the same man who thinks it's okay to set up a registry targeting Muslims, or who treats his employees like shit, or who doesn't care about families losing their homes.
Trump and Obama both love to golf. Plenty instances of taking celebrities, athletes out. Trump and Brady. Both guys and Tiger. I'd be pulling that card too if I were President.
I wouldn't, 'cause I don't give a shit who the president plays golf with. Again, though, a man golfing with celebrities doesn't exactly scream "See, regular middle America folks, I'm just like you!"
Onto the perception of Obama. I've stated that I think he will be remembered as a bad President. However, if had to pick an entourage of 4 Presidents to join me for a guys night out, he would be one of my top choices. Give me Obama, Clinton, JFK, And Teddy Roosevelt. I gather he loves to drink, watch sports, knows current pop culture. He stated back in 07' his favorite TV show was Entourage which I loved at the time. Seems like a fun guy and his ability to relate to people helped him in both elections.
I like many of those things about him, too (I don't care a whit about sports, but that's neither here nor there...). But I don't get why voters care so much about those particular aspects when it comes to deciding who to vote for, instead of just seeing them as neat bonuses. Yes, I want my president to relate to people...but I don't expect that relatability to come in the form of "Hey, he likes the same shows/music/sports teams I like!" or "He seems like someone I could have a beer with!" or whatever. Nice if that happens, sure, it's cool, but why does that matter?
Relatability, to me, comes in terms of understanding the struggles Americans are going through. And Obama grew up with a single mother. He watched her work hard to keep a roof over her family's head and see to it her son could get a good education. He is the very embodiment of the "American Dream" people like to harp on about.
Trump never had to work the way your average blue-collar worker did, or the way Obama did. He was born into wealth, he got things handed to him from his dad, and he has people do all the work for him. That is not something I can relate to, and I don't get how anyone in my economic bracket can relate to it.
Frankly, I don't think Trump's lifestyle is one people relate to so much as it's the kind they wish they had. And Trump, and the Republican Party in general, have led them to believe that they too can have this life if they make
just the right amount of money to do so...
...all while they keep pushing economic policies that will hurt those very voters more than it will help them, and keep them from achieving that dream life.
In Presidential practice, conservatives have complained about his elitist behavior. Aloof attitude. Way back he had his Deplorable moment when he referred to those in Middle America as bitter people who clinged to their guns and religion during a closed door Fundraiser in San Francisco. That was the root of the claims of his Cosmopolitan Elitism all the way back in 2008. Broadbrush statement, that is probably rooted in some truth, but every clinger must be judged on their own attitude.
He wasn't wrong about the "guns and religion" thing, though. Every time people even TRY and put forth any attempts at gun control, no matter how mild, we immediately hear people being all, "SECOND AMENDMENT RIGHTS! You can't take my guns away!"
And anytime people express any criticism of Christianity, or try and keep the separation of church and state, the religious conservatives throw a fit and talk about the "war on Christian family values".
Maybe every clinger has their variety of reasons why they do so, but what Obama said about them clinging, period, was a stone cold fact. And I'll remind you that I live in an area of the country where religion and guns are very important to a lot of people.
As for him being aloof...well, I'm a very quiet person offline. I hang back in conversations, I only really get more talkative when I feel comfortable around someone. I've heard about how people assume that quiet people are automatically "snobby" because they're not chatting up a storm when surrounded by other people, or because they might want some alone time now and again. Is that true, or is it just that some people's personalities affect the way they react in certain situations, or interact with people. There's been studies and discussion about how a lot of people don't seem to really understand the mindset of people who are more quiet/introverted/reserved/etc., and I sense that's part of the issue here.
Obama being "aloof" doesn't mean he's elitist. It just means he has a different way of communicating with people. And "aloof" can mean different things to different people, too. There's plenty of moments when he's appeared fairly social, too, and like you yourself said, he seems like a guy one can kick back and have a beer with, so it seems like he has some connection to people, which would kinda negate the "elitist" description, would it not?
There were moments when Obama seemed to really want to stick it to the American people. It was an elitist move to shut down the WWII memorial during the government shutdown. The memorial itself is an open-air charity funded monument in Washington. Maybe it was his 'Art of the Deal' to end the shutdown. But the ones hurt the most were veterans (some of them dying) who arranged to take group flights to DC to see the memorial. For me that was one of his lowest moments of smug elitism.
I'll refer you to the others' explanations here.
Other conservatives argue his narcissistic elitism is on display almost every time he gives a speech or press conference. Refers to himself as "I" in some deliveries more than 200 times. Those are a couple reasons why conservatives view Obama as elitist. The super-haters can cite many more, I'm not super hard on him (just a few moments). Every President will have those tone-deaf elite moments. Bush 41 in the supermarket check out line. Bill parsing the word "is". Trump is bound to have his moments too.
...every president has used the word "I" in speeches and talked about themselves at some point in their career, though? My goodness, if that's the metric people are using to claim someone's elitist, then we're
all elitist, apparently.
And that sort of "reasoning" is all the more hilarious when you look at Trump's speeches. Virtually every single one of them was him bragging on his riches and his wealth and how he was just the best at this and that and he's got grand, huge plans and blah, blah, blah. Obama's elitist for using the word "I" in speeches, but Trump can brag on himself all over the place and that's somehow okay and NOT elitist?
I grant your point at the beginning of your post that elitism isn't just tied to material possessions. This is true. But for conservatives/Republicans to sit there and complain that Obama's elitist while completely ignoring the blatant elitism in Trump's words and behavior is...laughable. And the height of hypocrisy. Which is why I'm inclined to believe the criticisms of Obama from the right have less to do with "elitism" and more to do with certain other things they refuse to acknowledge.
But we'll get into that when we get to the next part of the discussion.
Also, I hope you're feeling better.