We started Clerky exactly to solve this problem - as startup lawyers, every time we saw someone try to save money by doing paperwork on their own, there was some sort of issue with it. Yet we could definitely see why they wanted to do it on their own. So we built software to make it impossible to mess things up (as long as the information entered is correct).
It's hard to say why people reliably mess things up. I think part of it is that it requires of a level of attention to mundane details that is not natural to most of humanity. Another part of it is that it really helps to know some of the reasons behind why those mundane details are important - which requires some knowledge of how corporations work, contract law, etc. And it's one of those things where you don't know what you don't know.
Definitely a you don't know what you don't know and it's hard to test safely. Done wrong, this stuff doesn't immediately blow up in your face, that happens later, usually at some future inconvenient time.
I'm still sad that I don't have debuggers, test suites, sandbox environments etc for incorporation/legal work.
Can clerky do that for me?