My wording wasn't very clear here -- I didn't mean to compare middle-class Americans with ultra-Ortodox communities specifically, but to make a more general point about how people can consider themselves very free and really feel that way, even though things may look very different from an outside perspective.
Generally speaking, people feel unfree when they're suddenly constrained from doing something that they're used to and care about, or when constraints lower their status. In contrast, constraints that are ingrained in a culture are often not even noticed consciously by its people, or they are seen as self-evidently reasonable and necessary, since people are used to living under them, and are also at peace with the existing status hierarchy. However, this won't seem so to an outsider who is used to a different way of life and who perhaps derives status in his own community from some freedoms that are absent in their culture. Similarly, the level of discipline and regimentation (in both scope and intensity) is perceived subjectively depending on what one is used to.
So, ultimately, it depends on how you choose to measure freedom. In some extreme cases, it may be that one society is freer than another across the board, or very nearly so, for example if you compare modern-day U.S. with North Korea. [1] But usually, the impression greatly depends on what regime of constraints one is used to seeing as natural, and on one's subjective evaluation of the trade-offs involved. For example, many of those modern freedoms you mention are due to disappearance of strong informal communal norms that restrained people's behavior in the past, but as these social structures broke down, the necessary trade-off was the establishment and growth of impersonal bureaucracies that took over their necessary functions, and which now regulate, micromanage, and re-engineer practically all aspects of life and society. Whether you like this trade-off, and what you think of communities that preserved the older traditional modes of social organization, is of course your call.
[1] Though even this case might not be so clear-cut. Once I saw a documentary showing some illegal recordings of everyday life smuggled out of North Korea, and one of those showed a lady getting into a shouting match with a policeman, who eventually relented! In the U.S. this would be an invitation to get tazered, arrested, and likely charged. This of course doesn't mean that North Korea is not every bit as awful as people imagine -- if anything, it's probably even worse -- but this does suggest that some aspects of social regimentation may be more relaxed over there.
I was browsing my RSS feed, as one does, and came across a New York Times article, "A Village With the Numbers, Not the Image, of the Poorest Place", about the Satmar Hasidic Jews of Kiryas Joel (NY).
Their interest lies in their extraordinarily high birthrate & population growth, and their poverty - which are connected. From the article:
From Wikipedia:
Robin Hanson has argued that uploaded/emulated minds will establish a new Malthusian/Darwinian equilibrium in "IF UPLOADS COME FIRST: The crack of a future dawn" - an equilibrium in comparison to which our own economy will look like a delusive dreamtime of impossibly unfit and libertine behavior. The demographic transition will not last forever. But despite our own distaste for countless lives living at near-subsistence rather than our own extreme per-capita wealth (see the Repugnant Conclusion), those many lives will be happy ones (even amidst disaster).
So. Are the inhabitants of Kiryas Joel unhappy?