Objectivism

[genkaus]

This is where the system begins to become a bit paradoxical to me. So in the interests of charity one can give freely to a system if it gives them pleasure?

Pleasure is just one of the possible reasons. There may be many more.

How could a truly selfish person take pleasure from giving money they earned through their productive activity to another as an unearned handout?

By believing that the handout would be earned and returned manifold. Or the payment might be of a different kind altogether - for example, your children haven't earned the food or money you give them, but you gain pleasure from their use of it nevertheless.

I know that in theory it would be a freely willed gift on the part of the giver, not government "theft", but that does not adequetely place the motivation for such an action on egoist grounds.

I agree, the motivation present would not be enough. But that's not the same as no motivation being present.

It seems as though, within the Objectivist system, this presents a contradiction. It appears to be special pleading. In one circumstance it is deemed rationally neccessary to pursue one's own ends but to simultanaouesly exhibit compassion for another is to consider their ends as well.

No, to exhibit compassion is not necessary here. The compassion might be a consequence, but not a necessary consequence and according to objectivism - irrelevant to the man's moral nature.

As in it is more important to not give the government "my money" as opposed to letting someone die in the street because they lack health care that they can afford on their own.

Actually, whether giving the government "your money" is moral would be judged by the trade involved. For example, you may pay the government for the use of their police force, military etc and the government may use that money however it wishes. But that is not the case here.

As in it is in everyone's interest to provide safety net programs that the population, outside of once again the rich, will inevitably use.

How is it in the interest of the rich if they are not going to use it?

Plus on a practical level a charity system would never be able to sustain the sheer volume of elderly and disabled people who rely on the Social Security system for their daily monitary and medical needs.

It is the reliance on social security that needs to be phased out. Old age, accidents, disabilities are facts of life. Preparing for them is the rational thing to do. Expecting someone else to take care of you as a result of your own lack of foresight, is not.

Rand's justification appears to be ad hoc and she utilized the system in precisely the way it was intended to be used and to her own benefit. People will inevitably become old and utilize Medicare and Social Security. All except the rich, of course.

Actually, I find her explanation to be consistent with her philosophy. For example, she'd consider that all the rich people who were forced to contribute to the program, should claim from it once they get old - inspite of being rich. The system is not intended to be used this way - its intended to be used by those who need it - not those who contributed to it. Rand held that those who contributed had the greater right to use it. Therefore, your "except the rich" caveat does not apply.

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Objectivism has been hit many times for its lack of emotional textures,

And yet I find it to be emotionally exhilarating.

its illogical insistence that people will naturally do the best deeds when putting themselves first in every instance and its wholesale ball-polishing attitude toward capitalism.

There is no such insistence. The insistence is that they should be allowed to and pay for their own mistakes and misdeeds.

The fact that Rand herself could not tolerate the presence in her circle of people who, although fully supporting (in fact, doing so even in their own selfish actions) her philosophy's stated premises, rejected her ego on an amatory level suggests that even she was not able to tolerate the presence of a true individual.

You are mistaken if you think that it was only the rejection at amatory level that caused the Branden break. That played a big part - yes - but there were also other differences. Besides, Branden is only one case of many who have been rejected and you wouldn't claim that all were the result of unsuccessful affairs, would you?

Rand held her philosophy to be self-consistent and sound. So to reject any of its tenets was to reject its premises. Celebrating individualism does not mean you have to tolerate any individual who comes your way - especially not someone whose views are inconsistent with yours or who you believe is being intellectually dishonest. Since Rand believed what she did about her philosophy, its expected that she'd treat any deviation from its tenets as both of the above.