I don't understand how you compare "liberty" from one generation to the next. Especially, when you talk about positive liberty.
People with no money have better access to schools and healthcare . . . because others are forced to pay for their use of those services. Liberty up or down? I'd say down.
Plus, positive liberty opens the door to all sorts of other stuff: crime rates, rudeness, aesthetics, etc.
Again, I think the more interesting point is the libertarian and progressive refusal to admit that decay just might have occurred on at least one variable. Why is this so hard for these groups to acknowledge?
I thought I listed at least 1.5 things that are getting worse in my post. Clearly SIZE of government, and (according to the libertarian) therefore quality of governance is getting worse. Also, the repercussions of non-family-centric life scare me, as they should scare anyone who even remotely appreciates the conservative position ("it's mostly good now, please don't break it").
2. Positive liberty. Unambiguously up. Wikipedia:
Positive liberty refers to having the power and resources to act to fulfill one's own potential [...]
I, until I quit, am making a nominal $100K/y + bonus + pension + benefits, for 40-ish hours of work. Probably about $170K in pre-tax income. After tax (income, SS, Sales, etc.) and expenses necessary to do my job, that's down to about $100K (including benefits, pension, etc.). The other $70K is used 90% to feed the government monster, and 10% to increase positive liberty for a poor family. My positive liberty is down about 5% for what I am forced to give to the poor family. Their positive liberty is up about 40% because of what I am responsible for giving them. Massive net gain. I resent the hell out of the 90% going to feed the government monster, pay Goldman Sachs, pay Acorn, pay Congressman Rangel, pay a rich old guy's social security and medicaid so he can leave a $1M inheritance to his kids, rather than paying his own damn bills. I'm a lot less annoyed about the parts going to increase positive liberty for a poor family.
And I'm probably wrong. It's probably only about 1% going to poor, needy families, and 99% going to crappy, upward-distributing programs.
Still, my positive liberty makes my dad's positive liberty look weak, my grandpa's look feeble, and my great grandpa's look non-existent. The 1% to a poor family to increase their real positive liberty by 30% is NOTHING. The 99% to feed a ravenous government entity is about 98% waste.
I'm inclined to think that you don't appreciate poverty much...real poverty of the kind that exists in Africa or India, or even Mexico or the US of 1935. For quality of life, wealth (real, PPP-adjusted $) outvotes EVERYTHING else by a factor of 10:1 or better (Except wars, of which we haven't had a real one in 40-65 years, depending on what you count as real.)
Violence is massively down over the last 50 years, net. Rudeness is mostly old-fogeyism talking, and every old person since Hesiod has thought it was getting worse. Aesthetics is on the rise, massively. Read Postrel's The Substance of Style to explain.
On every measure of almost everything relevant to actual people who aren't mostly anti-change, damn near everything is up. Yes, there is Detroit, which is much worse than 1950. And there is Houston, which is much better. It's not ALL puppies and ponies, but it's so close as to be silly.
One more time: Government sucks more and more as it grows, and it's awful big now. Therefore Government quality is down (Sorry Grim, for being obstinate).
But Wealth is up, and therefore Positive Liberty is up. And the homicide rate has improved, the lifespan has improved, the healthspan is improving faster than the lifespan, the amount of beauty in the world has improved massively, people's work hours are down, people's housework hours are down, leisure is up, people are more attractive, IQ seems to have been rising for at least about 100 years (modestly), pollution is massively down, oil pollution including the gulf spill seems to be massively down compared to prior decades, air quality is better, forested area is larger...On what metric (besides size/quality/efficiency of government) are we less well off (excepting some tiny little pocket). I reserve the right to call bullshit on metrics (for instance, equality is down, but primarily because the internet boom let people get rich, not because anyone got poorer...I have a real hard time seeing that as bad). This year, unemployment is up, foreclosures are up, etc. Do we want to compare to a previous recession, or do we compare 5- or 10-year averages to be sane.
Remember, metrics, and country-wide...not opinions of 40 year old-fogeys like me, or cherry picked examples. And the fact that you DISAGREE with the aesthetics of Snooki gives you marks for taste in my book, but doesn't impress me as a metric.