Though I agree with the sentiment of your post...

> You concede your marriage suffered and suggest the impact on your health was negative, but both of these things could have happened if you were just surviving in a low paid regular job.

This isn't really a good way of thinking. Where will it end? You might as well do anything, since any negative outcome isn't necessarily inclusive of the thing you did.

I think it's more useful for second guessing your past choices.

You're absolutely right that it's worth weighing the chances looking forwards because it can guide your future choices.

But when looking back and thinking "if only I'd done this or that differently, everything would have gone well," that's torturing yourself with a imaginary timeline that never happened and for which there is a non-zero chance could have been worse.

While you shouldn’t torture yourself with past choices, you do need to recognize them so you can learn. They were a participant in the past it didn’t only just happen to them.

But they were already a programmer, so "low paid regular job" is extremely unlikely. Probably the "worst" they could have done was mid-level dev at a bank in the middle of nowhere making $65-80k/yr, which is certainly doable as half the household income to have a nice middle class life. The math changes in you're in a big city but the income does too.

It's easy to choose destroying your relationships and risking your health when the alternative is poverty. It's not so easy when the alternative is still making twice what the average American makes working in a cubicle at worst.