This is the result of decades of Republican lobbying, legislation and outright sabotage. The philosophy, openly advertised by Grover Norquist's Americans for Tax Reform, goes like this: nobody likes taxes. So if people find the filing process difficult and stressful every year, they will be constantly reminded of this fact. This will in turn make them more open to suggestions and propaganda along the lines of taxes being something that must be fought tooth and nail at every turn, because let's face it, who wants the tax code to become even more complex?
In contrast, if the process is streamlined every year, most people won't even pay attention to how much they pay in taxes - which isn't great if your ultimate goal is to keep government as small as possible.
The ease in which you can get away with these tactics ad infinitum is starting to make me a pessimist. It feels like it takes almost an entire population of unified people, that are diligently advocating on behalf of themselves, to compete with a ruling class that has the resources to stay on the offense forever.
The ruling class doesn't even have to actively communicate and conspire with one another (although they do). Their independent attempts to undermine and control government furthers the agenda of all private businesses.
It would help if Americans educated themselves on the basics of taxes. They would realize quickly how W-2 income employees pay a very high tax rate when you factor in FICA vs high wealth individuals who pay little to no FICA or income taxes. Add in the benefit of compound interest, cheap margin loans, and you have an incredibly unfair system. It's also why many wealthy individuals argue for a "smaller" government & less taxes. They travel private, go to private schools & prefer to avoid anything "public".
All this is with just the very basics, not counting step up basis, trusts or anything slightly complicated.
In contrast, if the process is streamlined every year, most people won't even pay attention to how much they pay in taxes - which isn't great if your ultimate goal is to keep government as small as possible.