I am in the OP category. I do not consider myself truly rich. In fact, relative to my neighbors and coworkers, I would say I'm about average.
I live in a nice house in a very nice neighborhood within a very nice town with excellent public schools and close proximity to a large city... but its about 2500 sq ft and on a 1/4 of an acre of land. So its no palace. My taxes are very high, but my mortgage isn't so bad because I plunked over 50% of the value of my house into a down payment. This left me cash strapped for a year or so, but I've built that back up to a comfortable level and it keeps increasing.
My wife is very chill... much more so then me. She shops for clothes for my young kids (under 4) largely at Target, sometimes JCrew or Gap if we want something nice for them. Why do you need anything better when they're just going to destroy them anyway? I mow my own lawn (only one in my neighborhood, but I think it sets a good example for my kids. I don't want them growing up thinking they can expect to buy themselves out of work). We used to have a cleaning lady once a week, then it went to once every other week, and now its not at all (when we were cash strapped, we got rid of her, and haven't added it back despite no longer being in a pinch).
Our biggest expense other then our house (mortgage, repairs, etc) and taxes is food and a club we belong to. I like golf and it was a good way to meet people in my town, so we splurged. Food is definitely an area where we spend more then an average family... we go out a lot, but that got very expensive and we have cut back from 3-4 times a week at $50-$100 a meal (you can't spend less, even at the cheap restaurants, for a family of 4 in my town) to a couple of times a month. This was purely because it was getting expensive... so we try and budget as well. Our attitude before was eating out was a default to cooking. Now we treat it a special occasion/luxury rather then an accepted default option.
We shop at Costco, and as I said, Target, and I rarely buy new clothes (basically get stuff for Christmas, and that's what I wear all year).
We save a lot of money, but I consider that for retirement (would like to retire young), and a lot of my pay comes in company stock. So although my income and net worth is growing and decently high relative to most in this country, outside of food, housing, taxes, and the aforementioned club, we probably live like a family making 100k rather then 500+k. And keep in mind, our housing is not extravagant. Its a type of house that someone making 100 or 200k could afford in a different area of the country.
I take issue with the tax agenda of Obama (and I am a democrat... but that is because of social reasons, not fiscal... though my social agenda will always trump my fiscal beliefs in voting). The reason why is the following:
Yes, I may make a good amount of money... more then 98% of Americans... but I consider the majority of that money as non-negotiable savings. In other words, I put a large chunk of money in the bank, and it STAYS there. NO MATTER WHAT. So I am living like someone making a fraction of what I make because I chose to SAVE. If I get taxed, you aren't eating into my disposable income, because in my mind, I don't have any. I have savings that don't get touched, and you're taxing my savings. So I don't live "rich" even though Obama would call me such. I really might as well not have 1/2 of my income on a given year, because its gone and stocked away. I'll grab it when I'm 45 or 50. The way I was raised, that is being responsible, and by repealing the Bush tax cuts, you're punishing me for my responsibility.
If I was making 50k a year, I wouldn't have a plasma tv, drive a BMW, buy a second home, leverage up my first one, and have no savings (all of which I don't do while making much more then that). I would figure out how to live on 30K so I could save 20k (clearly making the math easy and not talking about tax effects). I challenge many 50k per year households to say the same. My first job I made $42k and saved $10k while living in NYC. I was single, but still pretty good if you ask me. My thinking from those days has changed little.