Doing the tax equivalent of clerky.com is a "schlep" in PG parlance. It is EXCEEDINGLY difficult but it can be done. The number of people who can do this well

Doing the tax equivalent of clerky.com is a "schlep" in PG parlance. It is EXCEEDINGLY difficult but it can be done. The number of people who can do this well is probably very small -- take a few million words of ever-changing law, regulations, case law, etc. and convert it into code. Yet it has been done. Just look at tax return preparation software. It's out there. And it is, for the most part, shit. I offer that judgment as a tax lawyer whose office prepares tax returns. And who cleans up messes created by people using the software out there in the world. Tax software alone is not the end to shoot for, however. You need to bolt together a bank plus accounting software plus the tax software. If you have a fashion-forward bank that will host a better Quickbooks (not just "oh, yeah, my bank talks to your software" -- make it F-ing work), then have that accounting data speak directly to the tax software -- this is a winner. For extra added bonus points, this system collects all of the documentation required by the IRS on audit. For the bulk of people out there, tax and accounting is a schlep problem and not a brain damaging intellectual exercise. And if you solve 80% of the problems leaving 20% for the owner/accountant to solve, you've saved a ton of time and money. I have been cobbling together a system for nonresident consulting types to do business in the USA: a corporation, how to sign the contracts with consulting clients, how to allocate the income to taxable in the USA vs. not taxable in the USA, how to pay the employees/consultants properly in the USA, what paperwork to file, etc. etc. But it has humans where software would be useful. That's because of one key constraint. The biggest problem is that people don't want to do the schlep work -- not even download data from the credit card or bank sites into their software. And if they download, they don't want to look at it. They'd rather allow magic to occur. Someone should write magic software. :-) It's either magic software or intelligent and expensive humans.