Or you could just have the government itself develop the software in tandem with the tax regulations. Obviously, even that would still be easier and cheaper with a less complex tax code, but in this thread we're talking about "open source tax software" that shouldn't even really need to exist when the government could just provide a fully functional web portal where the corner cases have been tested exhaustively by the organisation that knows those corner cases better than anyone.
This has to be the most sensible thing. The UK used to say that "tax doesn't have to be taxing", very pithy but then I tried to make a zero return for a dormant company and had to use some horrific software from the HMRC (tax office), which was some weird XML thing that was impossible to understand.
If the government had to make the software we all had to use, as well as it being free, it would force the government to consider the cost of modifications when they decide in their infinite wisdom that some new tax-break should be created.
Inertia can be good to slow-down knee-jerk politics.