From Ability to Needs

After some study on the subject Socialism, I have come to some conclusions, but maybe even more questions. I begin this line of questioning that I may have a better understanding of it. Let's begin with observations then move on to the questions:

To me, the basis of Socialism seems to be the underlying assumption that man is a social creature that progresses in society better as a whole. That the individuality of the person is discouraged so that he may better utilize his skills to serve the community. The security, health, and care falls on the collective instead of the individual.

To me, placing the community above yourself and your family is not a trait naturally found in man. We all agree that man is fallible and corruptible, you can use religious or historical texts and find the percentage of actually good people to be quite small. Unquestioned and unchallenged authority more often than not leads to some form of dictatorship.

My question is this, can you ever really take the individuality out of a person? Does Socialism and Capitalism really boil down to this one difference? Is it my stuff or our stuff? What of the person who is in charge of handing out the communal stuff? What is in place to guarantee the stuff gets handed out exactly and only according to needs? How do we keep that system from turning into one of favors and priviledges? Why is it that in past socialist experiments, the end result was always one where there was a ruling and favored class at the expense of the community? Who is in charge of a socialist community? Is it the collective and do they vote on everything? Do they always elect a leader and if so, is that contradictory to socialism? Does Socialism believe in the inherent "goodness" in man? The best case I have come across was the Jewish Kibbutz, that did have a communal approach but ended after the government stopped subsidizing the communes. Even at the end, the Kibbutz members had their own clothes, food, and other items.

Is it as black and white as, "Is man an Individualist or a Collectivist?" Are there any in betweens? Because we can all agree that man is a social animal. He would not be able to farm, fish, and build his shelter if he were by himself. So he needs the support of the community. But is that individual drive to better his position for safety, security, and, dare I say, social standing, necessarily a bad thing?