You can't really automate lawyers, unfortunately, anymore than you can automate accountants. Someone has to assume the liability for giving you legal advice / accounting advice. Computers can't yet assume such liability.
I see two ways around this:
1. The company behind the computer takes full responsibility and charges for the risk. Stripe has made online payments a breeze, because they are the one taking responsibility for the legal things (securing payments, proofing physical access to servers holding the credit card data etc).
2. The tool is so understandable that I'm willing to take the legal risk. There are a few tools that make accounting so easy for a small business owner that I'm willing to take the legal risk myself about the accounting.