I don't see how Tim's conclusions follow from his premises.
If we are supposed to think of general taxation and the overall amount of government spending as reasonably justified on the grounds that these things were the outcome of a democratic process which "the people" (somewhat indirectly) agreed on, doesn't the same logic suggest that the loopholes are similarly reasonable and justified?
Loopholes aren't a bug in an otherwise perfect system; they are part of the negotiating process that produces laws. If it weren't for the loopholes, legislators wouldn't be able to find support for tax rates as high as they are. The loopholes are there for a reason. The loopholes are part of the exact same "social contract" that produced the taxes.
No, that would be overly relativistic. There is a huge corporate culture that drives tax law lobbying. This has created a situation where tax law more likely reveals the will of the corporations, not the will of the people.