I agree completely. I wasn't really expressing a quandary, but rather reflecting on the fact that liberties often allow things that, while legal, aren't moral.
You point out that: "The right to discriminate against person who has the proper information, credit, and money to rent an apartment, infringes on that persons right to live where they want in a free society."
But in response, I could point out that requiring someone to rent their property according to predetermined legal qualifications, presupposes jurisdiction over the use of that property, and the operation of business in general. And I question where such jurisdiction is derived.
Once private property is involved, where does the privacy end, and the social obligation begin? The basic premise is that the limitation of accessibility of any private property towards any particular person, does not deprive that person of access to other property, and so does not deprive them of freedom. Otherwise, there would be no private property rights at all.
An example is Free Republic itself, and it's ban on liberal arguments, lawfully made through it's private ownership. Yet, at the same time, that private ownership would not allow restrictions based on race.
That's where the 14th Amendment causes so many problems, because while used to justify protection against racism and "inequality," it does so by creating the legal mechanism of privilege in replacements of rights. And once fundamental freedoms were jurisdictionally transformed into limited privileges, Pandora's Box was opened, and there has been no end to the trouble that's resulted from it.
The original Constitution is about nothing but privacy and equality. Thus freeing the slaves merely required their explicit acknowledgement as included in the definition of "the People." Instead, we got the Civil War Amendments and had our rights presumed into privileges.
You could have fooled me, I read McCain, Romney threads here all the time.