Does Mitt Romney have an image problem? Yes. Is it rooted in envy? Not so much.
I'm writing this as a believing Latter-day Saint. I also voted for Obama 4 years ago, and intend to vote for him again in November, so maybe you want to take this with a grain of salt. But here goes...
I'm not fond of Mitt Romney as a candidate. As a Latter-day saint, I'm more than willing to give him the benefit of the doubt. I know how hard church leaders and church members work, and how much they serve. I know the emphasis placed on charity, honesty, and loving one's neighbor. I know from experience that most church leaders are sincere in this. They agonize with and over those who struggle, and often move mountains in trying to help them. I also know that every couple of years, Brother Romney sits down with his priesthood leaders and has a talk about his own worthiness. One of the questions he is asked in that situation is whether he is honest in his dealings with his fellowmen. So on a personal level, I'm willing to say that Brother Romney is probably a pretty good guy. I don't know him personally, but I feel on some level that I don't have to to be able to make that kind of judgement. That feeling comes from both of us being Latter-day Saints. So, that said, why don't I support him as a candidate? There's a disconnect between the way I perceive him as a person and how I perceive him as a candidate, and that gives me pause. I see problems on three major issues: the issue of privilege, the issue of integrity, and the issue of honesty.
First, the issue of privilege. There is no doubt in my mind that Mr. Romney is a hard worker. I'm sure that his success in life would not have been possible if that weren't the case. On the other hand, I think it's foolish to say that his success in life is purely derived from his gumption and hard work. Mr. Romney was born into a wealthy and powerful family. They were well connected in both politics and business. Regardless of what Mr. Romney did with his inheritance, his father's position and connections opened doors and built a network for him in ways that are simply unavailable to most people.
Now, life is not fair. Some people win the genetic lottery, and some people win the family lottery. That's the world we live in, and even though it's regrettable for those people who are born with fewer advantages than others, it's not particularly problematic. Or at least, those who do view it as problematic are also forced to admit that it's impossible to change without sweeping, radical changes to society and or biology. The problem arises in Mr. Romney's case because he seems unable to imagine life without those advantages. That leads to a line of thinking: "I am successful due to my own efforts. If you are not as successful as I am, it is because you have not worked as hard." Put more harshly, if you are unemployed or underemployed, it's entirely your own fault. Quit whining and get a job, or a better job. If you start a business and it fails, or doesn't wildly succeed, it's entirely your fault. Luck plays no role. Timing plays no role. And so on.
Most people, I think, recognize that hard work and initiative are necessary, but not sufficient for success. That Mr. Romney seems to be suggesting otherwise is, I think, problematic to some voters (including myself). Now, it's possible that he has a more balanced and humble view of his own successes, but if that is the case, I don't think he has articulated it well.
The second issue is one of integrity, you would think that this would be easy for Mr. Romney, since he is running at least partly on his moral fiber as a religious man and church leader. Unfortunately, he has a history of changing his positions on issues too frequently and too easily. I understand that people can change their minds. I understand that there are often nuances in political reasoning (e.g., it's possible to believe one way and appear to vote another because of subtle details in the wording of a particular bill). I also understand that in functioning representative governments, there is often a need to compromise, which could possibly lead to apparent inconsistencies if votes are examined out of context. In Mr. Romney's case, though, none of these situations seem to apply. To me, as an outsider, it looks as though he is simply a chameleon, trying to change his positions to be whatever he thinks the electorate wants. This becomes problematic when we ask the question: if he is elected in November, which Mitt Romney will we have put in the White House? Will he be the moderate Mitt Romney who was governor of Massachusetts? Or will he be the much more conservative Mitt Romney who has appeared during the campaign? Or, having achieved his goal of the White House, will he be a third, entirely different Mitt Romney we haven't yet met?
Lastly, the question of honesty. Again, you would think this would be easy for Mr. Romney and his campaign. As I noted above, Brother Romney is called to account for his honesty every couple of years when he renews his temple recommend. It's probably true that Mr. Romney is personally honest. However, when I hear his voice saying "I approve this message" following statements which are at best misleading and at worst explicitly deceptive; when I see that he chose as his running mate a man whose convention speech was called out by Fox News (!!!) as being "an apparent attempt to set the world record for the greatest number of blatant lies and misrepresentations slipped into a single political speech" ; when I hear a pollster working for Mr. Romney's campaign say, “We’re not going to let our campaign be dictated by fact-checkers,” I'm forced to wonder whether he's in control of his campaign, or if he just employs different standards in winning elections than he does in his personal life.
Any, or all, of these things may be off the mark. It's possible that I'm not seeing all of the facts, or seeing the facts in a skewed way. But that's not really important, because what I'm talking about here is an image problem. Mr. Romney's degree of personal honesty doesn't matter if the voters perceive him to be dishonest. The actual degree of his commitment to a particular set of political principles doesn't matter if the voters see him as someone willing to adopt any position simply to get elected. And, the degree to which he does or does not acknowledge the benefits inherent in his privileged upbringing does not matter if the voters get a different message.