The biggest obstacle that I can think of, is that all the BTC transaction is not traceable, thus government have no way to collect tax in whatever transaction, then it's purely depend on individual merchants's honesty in paying the tax
Or maybe bitcoin just suit a society without any tax at all, so we have to buy insurance for everything basically covered by government today: health care, education, retirement, jobless compensation, road and infrastructure, etc...
You know, first they ARE tracable, second this has not stopped cash businesses from being taxes for many many hundreds of years