As for investing pensions in the stock market, I'll merely add that in Australia, where we've had superannuation for 20 -odd years, all usually invested in stocks, there were are a large number of people who thought they were going to retire in 2008 (my parents amongst them) who are now still working.
Psychologically, does it work? In general, if you tell a 22-year-old that in 40-something years he's going to really need some of the money he's making now (even if he feels like he's barely paying his bills), that he absolutely must set aside enough (and invest it wisely, assuming he has the wisdom to do so), will he manage to do it?
From what I understand of human psychology, the answer isn't "yes" nearly enough to make your solution palatable.
It sets up a good learning experience for him when he finally gets to retirement age and finds himself as a greeter in Walmart, but it's way, way too late at that point.
No one wore seatbelts before they were legally required (and still many don't, and many still die because of that dumb decision). People don't, as a rule, have a good grasp of the distant future and/or events that seem unlikely. How many people are still starting smoking, even though it says "cigarettes kill" in big black letters on that first pack they buy?
There are plenty of problems with the US social security system, but removing the safety net entirely to teach a lesson to people who fail to adequately prepare for their old age doesn't feel like a sound approach to me.
Do you support alcohol prohibition? Alcohol leads to much more damage than even smoking from an emotional and psychological perspective.
What if, one day, the government decides that people who buy Japanese cars are a danger to themselves since they are costing the American car companies so much money by refusing to buy home-grown goods? The people just don't have the foresight to understand that buying Honda today means depression throughout Michigan tomorrow. Shouldn't we protect people from that eventuality by ensuring that they only buy domestic vehicles?
How far do we take this? Why do we believe that the politicians have such a heightened sense of foresight and such impeccably unselfish motives? I don't vote for people so they can do my thinking for me, I vote for people who I think will best represent important core principles, like retaining individual free exercise of conscience (like the choice to buy American or foreign cars, even if it will cost Michigan a lot of jobs).
The attitude that we need the government to protect us from our own decisions is in fact extremely dangerous and insidious. Old people survived for thousands of years before the implementation of social security -- if the industrial society doesn't support old people well enough, we have to tweak it so that these things work instead of doing these grotesque hacks of taking > 10% of an average person's salary every year to pay to support your grandpa's RV tour of the US.
This is partly why I hate political discussions as-they-are-played... everyone has such strong opinions based on incredibly tenuous links to actual history, studies, etc.. Just "this is how it is, how it has always been, and if only I were in control I'd have this all tidied up right quick."
Of course I don't support alcohol prohibition. Haven't we tried that? Did it work? Also: we weren't talking about making smoking illegal, just about human psychology, and how people aren't logical. To actually give people better lives requires science, not "more laws" or "fewer laws".
I don't disagree with you on your other examples, generally, but I'll refrain from offering other examples that are obvious in the other direction... it doesn't get us very far.
"I don't vote for people so they can do my thinking for me" -- I half agree with this. I will gladly vote for someone who has thought and researched more deeply on important topics than I have, provided they can explain themselves and advance my own knowledge. In the end we are responsible as citizens for who we elect, so I do agree it's not much use to be snowed by anyone who uses big words or says they have the solutions.
For core principles, though... this is much trickier. Principles, in abstract, are useless. I agree totally with some of my older relatives' politics, when we talk only in terms of principles ("we need better education! critical thinking!"), but when we get into applying the principles we're miles apart.
"Free exercise of conscience", what does that mean in terms of specific issues? We should rely on lynch mobs instead of police? Citizen militias to take out unfair monopolies?
I'm in favor of encouraging responsible citizens who can think critically. I'm not at all convinced that your suggestions (inasmuch as I've seen them) would do that, based on what I know of human psychology.
I also have a suspicion that your idea of what social security payments will cover is a bit overblown. I don't have any living grandparents left, but my father is losing his house and has no medical insurance, in spite of social security.
While there is some migration to the richest province, that has more to do with jobs related to the oil boom there, and the low taxes there are due to oil revenues.
A good reason not to trust the government to keep a forced retirement account on your behalf. Someone is going to get the short end of the stick here eventually.
I would prefer that people own up to this and we set up an orderly, phased dismantling of the program, but that doesn't seem very likely. Politicians and head-in-the-sand populace apparently insist on a single disastrous collapse that leaves millions insolvent rather than admitting and accepting that there will be some controlled loss involved in a phaseout.