Incomplete Article on Charity

Regarding the claim:

"In freedom, not enough people will give to charity so that the disadvantaged of society are reasonably taken care of. Therefore, the government must take wealth from the rich and give it to the poor. Alternatively, giving to charity could be incentivized through tax policy."

Responses:

1) Positive claim needs evidence badly.
Freedom is the default position of civilization, as a whole or any piece of it, and any claims that some enslavement (redistributing wealth or taxing) is needed should be critically considered. Critical thinking usually requires evidence.
Historically, people have given to charity regardless of government involvement for thousands of years, and most of these people have been middle class or poor themselves (by living standards at those times). The vast majority of humanity has always been religious, and the prominent religions of nearly every era have strongly encouraged giving to the poor or made it an outright moral obligation (more on that later).
In more recent times, secular friendly/fraternal societies offered medical/emergency services and unexpected unemployment/death in the family assistance to its members using a community organization model with members pooling what resources they had to help each other rather than a business model for funding. Additionally, these societies were very active in their community often raising funds for fire and police departments, churches, schools, scholarships, etc. While some of these friendly societies still exist today, most of them have been crowded out by government programs started by Hoover and FDR and then expanded by their contemporaries. All of these government programs are far less effective and efficient than the friendly socieites that they replaced, placing a huge burden on the tax payer and eliminating vital services for every community (more on that later).
Up until HMO's were introduced, most hospitals worked with patients to make payment plans to pay for expensive procedures, or the hospitals were charity organizations themselves often asking patients to pay what they could but would never refuse service based on an inability to pay. While a few of these charity hospitals still exist today, government funding and regulation of hospitals, as well as medical insurance requirements and regulations, have made reasonable prices impossible and most charity unfeasable. A common response to high medical prices and the disappearance of charity hospitals is universal healthcare and/or forcing all hospitals and doctors to treat patients even if they can't pay, both of which come with their own counter-productive economic consequences (more on that later).
Lastly, people still give to the poor and to charity organizations even when tax policy is inapplicable, not just monetarily, but through volunteering time and resources (ex: free use of a venue for fund raising).
If there is any historical evidence at all that freedom is incapable of helping poor people it is weak at best.

2) Welfare Economics

3) Morality

4) Sky is the limit?
Let's assume that there is sufficient evidence that we need a little enslavement to take care of the poor, or no evidence is required due to moral considerations, or we accept welfare economic theory.
Not enough people. Disadvantaged. Reasonably taken care of. Rich. Poor.
All of these statements require a decision. To whom does this apply, and to what degree? Who will be making these decisions? If we are taking the political route, then with the current government system the people making these decisions are going to be politicians and bureaucrats.
Politicians are influenced by the rich and powerful and are not influenced at all by the middle class and working poor. It is often the case that politicians, when forming new legislation, will seek out consultation from the very businessmen, corporations, or 'rich people' that the political act in question was intended to tax, punish, or regulate in the first place.
Bureaucrats are always looking to expand their departments and budgets, and to justify their continued existance. In the case of welfare, this means give out as many benefits to as many people as possible and under no circumstances should a recipient ever stop claiming those benefits, such as a person finally pulling themselves out of poverty.
These are not failures of our specific arrangement of the political system, these are inescapable features of democracy, a representative republic, and bureaucracy. This means the rich will avoid redistribution, the middle class and working poor will be targeted for redistribution, they will pay for the lavish pay, benefits, and pensions of the bureaucrats, and the disadvantaged are encouraged to stay poor and never become contributors to society (which is what we have now).