(1) The substance of the paperwork will never be simple, as long as the industries directly dependent on complicated Federal taxation law, tax attorneys, accountants, can buy politicians.
(2) The online nature of filling out the virtual paperwork will never properly function as long as elected politicians think they have to dole out the job based on political and ethnic concerns, i.e. H-1B. Remember the ObamaDontCare online presence? When it first went online, and failed so badly, a trio of 20-year olds within a matter of 48 hours built a website that replicated its functionality to a tee and worked flawlessly.
Now, if you really do want taxes to be that simple and that easy, seek, find, hug and support your nearest neoreactionary.