Author here, hope you enjoy reading this. Feel free to ask anything. thanks
I like the gist of this approach. A few years ago, I read about some books of the legendary (non-software) engineering projects in the past. Engineers were very cognizant of risk and costs, far more than I see in software practice. With some reflection, I think that's just a defect on our field's part, not and not only because the software game is different.
I think a lot of it has to do with the lack of understanding non technical people have with the relative difficulty of software tasks. Building a 10 foot bridge is clearly much easier than building a 100 foot bridge, but in software it's murkier.
Write a program that checks the rank of a poker hand: okay, give me an hour or two. Now can you change it so that it checks the rank of a photo of a poker hand? That should only take you like 2 or 3 times longer, right? Oh, more? Well I'll give you a week, that should be plenty.