Earlier quoted context omitted.
I think the meat of your comment is in the story about how Citibank's failure makes it harder for you to find a job. First, note that if it weren't for regulators deciding on the amount of reserve capital Citibank was required to hold, the market would probably have demanded that it hold much more. For a long time iBanks have been benefiting from the Fed's power to bail them out. Unlike banks, whose asymmetric liquid…
I have serious trouble believing that "the market" would have led to Citi keeping larger amounts of reserve capital around. In fact, I'm pretty sure that it was the banks pressuring the government to let them hold less in reserve. I am registered Libertarian, as I believe in marketizing problems whenever possible; however, the markets must be set up correctly to be truly free, and only the government can do that.
The psychology people seem to have is to believe that if the government regulates it, then anything that falls under the regulation requires no independent thought.
On the icy road, the safe speed maximum is probably about 30 mph, but many accidents are caused by people going the posted limit, as people seem to trust the wise planner above their own ability to judge.
Similarly, people assume that a firm that is regulated by the SEC and backed buy the FDIC is going to be a safe place to put money, which is not always true.
I agree with your last statement, but note that 1) the SEC required insufficient reserves, and 2) because the government set the reserve limits, there is the implication that it ought to bail out the firms that were "just following the rules".
Hence the view of firms being "too big to fail" comes from the idea that regulation is perfect and if only it's followed then everything will be fine.
In a better, more libertarian world, banking crises would result in some failures, and once-burned investors would look carefully at what reserves actually mean, look sceptically at rating-weighted reserve requirements, and expect that if things go wrong there will not be a bailout.
This would help put money into firms that actually know how to act in a trustworthy, sound way, not just the firms that are able to successfully lobby the SEC, the way Madoff's did.