Hi. Interesting topic. I'm joining in rather late, but I felt compelled to throw in my 2 cents. I didn't get to read the entire thread, so I may be repeating someone else's opinions.
First off, some background about my experience: I've lived in a communist country (Romania) for 12 years. Now I live in Canada. This February I went to Cuba for a week on vacation, and travelled through some of the cities and towns between Santa Clara and Caibarien. Although my experience there was fairly superficial, I did recognize right away a number of traits that I've see before, growing up.
The biggest problem that I see with socialism is that it inadvertedly promotes laziness. I've seen this happen in Romania, in Canada, and in Cuba as well. People become accustomed to think that their problems will be taken care of by the rest of the community/government, so they become lazy in a large number of ways. Progress inevitably comes to a halt. Garbage ends up dumped on the street, people remain complacent on welfare cheques, and invention and innovation stay at a minimum. I live in Ottawa right now, where most jobs are in the government sector. Everyone knows how wasteful things are there, with people getting paid large salaries for going to get a paper signed at 10 AM, and returning with it at 4:30, just before getting ready to go home. If anyone rolls up their sleeves and works harder than everyone else, they get scorned.
The other big problem I see is in the absolutely false notion that everyone is created equal, and that therefore we should redistribute the wealth from the rich to the poor. People are only equal in the sense that we all have the same basic human rights. However, every person is an individual, with their own personality, strengths, and weaknesses. If someone works hard AND smart throughout their life, and gets rewarded for it significantly more than others, why should this person be punished by being forced to give up a larger part of their reward for the good of everyone else? This person should be free to do whatever he or she wishes with the fruits of their labour, as long as they don't infringe on other people's rights.
I've seen a lot of poor, or struggling people who work hard all day, and yet they barely manage to have enough. Many of them think it's unfair. They think they work harder than other people who are much richer than they are, and that therefore they should get their "fair" share. A big problem is that the kind of hard work that they put in may only be of a very small benefit for the community/market, and therefore be of low value to the rest of this community. Someone could be working hard all day scrubbing toilets, and be absolutely exhausted by the end of it, and yet, frankly, the market value of this work is much smaller than someone who works only 3-4 hours a day managing a 3000 person company. The skills required to scrub toilets are simply of significantly smaller value than the skills required to sucessfuly build and manage a large company.
The last big problem that I have with socialism is that it creates a huge Big Brother government under the guise of "people power". Inevitably, when power and money get concentrated into this government, it creates a sort of large black hole, where all that goes in doesn't seem to come back out. It seems to me absolute folly to think that someone up there in government knows better than you or me how to lead our own lives. Anyone who tries to convince other people of that is a big liar and a swindler. People who serve in government are NOT Gods. In most cases they are people who are more interested in personal power than in the good of everyone else. They are called politicians. If you give this body of politicians the power over everything in the community/country, then it's like investing with Bernie Madoff.
Ideologically speaking, socialism favours the community over the individual. However, in real life, erasing the individual has always proven to be an abomination. It happened with Nazi Germany, Communist China, Communist Russia, etc. A lot of people nowdays seem to forget what "Nazi" stood for - National Socialist Party. Humans are individuals. We feel and think as an individual, and we prefer to interact and live in a community. This will continue to be the case for at least centuries to come, seeing as it hasn't changed in the past few thousand years.
Now, my personal preference is for something along the lines of libertarianism, and true free-market economics like the Austrian school advocates. The economic system in the US is anything BUT free-market, so I would definitely stay away from it. In a free-market system, the market is the one that determines the value of products and services, NOT the government or any private entity. Essentially, the market truly is the wish of the people, since it's their supply and demand that comprises it. This goes to show that a true free-market would be the ideal system, since it would truly benefit everyone FAIRLY. Socialists tend to think it is a harsh and unfair world, and they want to artificially make it "better" by forced control. As soon as the market is forced artificially in one direction or another, THAT is when things become unfair for one group of people or another. This is basically how monopolies start in the large majority of cases - through government interference.
The economy in the US right now is controlled by certain banks, through fractional reserve banking and the Federal Reserve (which is a private bank, NOT owned or controlled by the people). They hold a monopoly over the money supply, and the people have no say in it. A large number of problems in their society stem from this fact. The same is the case for a large number of other countries that operate in a similar fashion (money supply is in the control of a private Central Bank). This is not free market anymore. It's a big swindle.
Whoever in the US or Canada thinks that they're paying income tax for the good of the community is either naive or delusional. Not only does the income tax violate our basic human right to the fruits of our labour, but it is used to pay off the interest on the money that government borrows from the Private Banks (which should be created by the people with no interest at all). Forcing people to pay income tax is basically saying that the government OWNS 100% of our income, and that it decides to let us keep a certain percentage. Education is truly lacking in our society today.
Anyway, that was my 2 cents 
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