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yes and no. when discussing issues of freedom, it always gets murky as there are different shades and view of exactly what we want to be free from. as a progressive (which I view as being both compatible with conservatism and liberalism) to me, the question is "free from what?". In the end, we are all subject to frailties that physical existence subjects ourselves to from instinctual drives, to biological, to emotional, to spiritual, to social needs (and other categories), which in the end makes us subjects or something whether we like it or not. some traditions of liberalism like to make a distinction between society and the individual in some cases, but I personally don't see the need for it and such a distinction as being wholly artificial. Some would promote the idea that this distinction is where the line to freedom truly is. but even then we are still subject to all sorts of forces and are our lives any better as a result?
that question, obviously is unanswerable as there is no determinism in what it asks. it simply states that without one force, we are simply better off in a metaphysical sense that may or may not control for practical benefits. so yes, modern liberalism offers freedom and so does old school liberalism, and frankly so does theocracy, communism, and any other ism, its just a matter of "which freedom". Even despotism offers freedom from the burden of choice (which can be attractive for a higher % of the population than most would suspect, unfortunately) and certain types of consequences.
In the end, we are just a mess and bundle of drives and needs a smattering of logic thrown on top for self justification and rationalization. which freedom is best? I personally am not sure. I don't see the old models as realistic, but idealistic in light of what we know about how the brain functions, yet at the same time, there is use for high expectations and stretch goals as it brings out the best in people (but then the libertarians would be in horror in that i would even see their philosophy as only useful in the same practical and social engineering considerations I see in the use of any philosophy) in certain ways, but it also brings out the worst in people as well.
So in a sense mill had it right and wrong as there is no clear standard because humans just ain't built with a single overriding drive, but a mix of competing drives which is what gives rise to all styles of political philosophy in the first place.
Exactly. All of this is ultimately put together in various different shades of gray. How objectively "desirable" any given system happens to be all depends, in the end, on what you are trying to accomplish.
While I personally lean a bit more towards the very mildly Libertarian side of things in my ideology, I am fully willing to admit that systems which provide greater or lesser degrees of freedom can be preferable under certain circumstances. For instance, during the Dark Ages, an authoritarian government which provided a person "freedom" from fear and harm in a dangerous world was preferable to democracy.
Today, there isn't as much of a need for that kind of thing, so our society has shifted to provide a much greater level of personal and political autonomy. There is nothing wrong with that.
Practicality ultimately determines what the "best" system, and the best degree of "freedom," for any given situation happens to be, IMO.
Unfortunately, however; it simply happens to be the case that people will occasionally get it wrong, and wind up supporting a broken and unsustainable system as a consequence of this. When this happens, the results generally tend to be disastrous on a long term basis.