The one point I don’t completely understand is the tax debt: Wouldn’t a failed business, no matter how ridiculous, be a complete write-off?

Maybe the problem is that he has to tax each fiscal year independently, so a tax debt in 2023 from successful freelance work would not be diminished by a failed “business idea” in 2024.

This is a crazy use of AI!

What I have been considering, but haven’t found a readily available setup yet: Make a user with lots of read permissions (most of /etc, API keys & passwords in separate excluded files). That could be done with very restrictive sudo patterns. Let the AI run commands under that user directly (it can do sudo -l to get an idea of what it can do). Then, use it like in Star Trek “Computer - run a level 2 diagnostic”.

Not as the centre of attention when fixing a problem, but as additional input / modern rubber ducking.