All of this is a really interesting discussion about political theory, but it seems to me that whether one is a hypocrite rests on the answer to this question:
Should a person of your income level, living under our current political system, with all its flaws and imperfections, pay more money in taxes than you currently do?
If your answer is yes, then taking legal tax breaks is inconsistent with this principle. If it is no, then legal tax breaks are not at all hypocritical. It's as simple as that.
What's interesting is a lot of this thread has been about why the answer to that question is no. Which begs the next question: should anyone be paying more? If yes, who? But it seems to me like that's a whole separate, more complicated, discussion.
Nope, not at all. I am willing to pay more in taxes
to fund programs that don't exist. E.g., I am a fan of ACA and have been fine paying the surcharges that fund that. I would vote to tax myself more heavily to fund shoring up SS. Etc. Where the government has elected not to pursue those priorities, I will pursue on my own through charity vs. voluntarily sending more money to the government.
I think there is a real false dichotomy here that being liberal means that you must either voluntarily devote all your resources to others, and if you say "enough," you're a hypocrite. That's bullshit, in the same way that "conservatives are just greedy bastards who want to keep all their money for themselves" is. The key for every individual, liberal or conservative, is to figure out the appropriate balance in your life between what you dedicate to your own private good and what you dedicate to the public good. And the "public good" portion of that includes both goverment and charity, and it includes contributions that are made via both money and time.
I think there are liberal/conservative splits under all aspects of this. I suspect the clearest liberal/conservative split is whether the "public good" should be accomplished through government efforts vs. private charity. I suspect there is also somewhat of a liberal/conservative split on the overall question of how we apportion resources between public good vs private good overall (e.g., the libertarian view that the best way to achieve public good is to maximize individual autonomy); however, I think this latter category varies more by individual (e.g., I know many conservatives who believe very strongly in small government and low taxes, but who contribute generously to charity).
Personally, I am a liberal, and I believe there should be more government action vs relying on private charity. I also pay probably 1/3 my gross income to the public good, between the taxes that I pay and the charitable donations that I make. But there's no magic number here -- no, "whew, I'm safely out of the Hypocrite Zone" level, or "damn, I'd better up my game" threshold. Personally, I'd be willing to shift that 1/3 higher to shore up SS or institute single-payer health care. But we don't have those things, and so I think that balance is quite sufficient for now, thanks very much. OTOH, if the ACA goes away, then I probably have to tip the balance more towards the "private good" aspect, because that means I need to save more for my own future medical cost. Etc. YMMV.
And it doesn't beg the question, it raises it. ;-)