> If you give someone a little shove, they bump their head, and they die

What you're describing is manslaughter or possibly not a crime in most jurisdictions, but your point stands. Generally, murder is an intentional killing, and manslaughter is an accidental killing. But if, say, you give an aggressive drunk a little shove and they bump their head and die, you probably haven't committed a crime. Nonetheless, luck absolutely plays a role in punishment in our current justice system in a thousand different ways. I don't think most people consider the element of luck to be ideal so much as an unfortunate but necessary reality.

With the eggshell skull doctrine, you're talking about paying for damages in a civil case. I think most people see reparations differently than punishment. In civil law, you pay to fix the damage you caused, even though the exact amount comes down to luck. But criminal punishments require some criminal intent. It's a higher bar.

> there is some reasonable assumption that when taking a wallet you are at most stealing a few thousand dollars

I think you're giving thieves too much credit here. They may not expect most wallets to have more than $1000, but I don't think most thieves have some innate goodness in them that makes them want to get a wallet with less than $1000. I think it's the opposite: if thieves knew someone had $1B in their wallet, and the chance of getting caught was the same as stealing any other wallet, I think most thieves would want to steal that wallet more, not less. And I don't think most would care if the money in that wallet rightfully belonged to the investors of Madoff Investment Securities either.

> factors like pre-meditative effort or degree of remorse ... moment of weakness

With these factors, you're judging the thief based on their character. We're both advocating this. The difference is you're arguing someone who steals a larger amount of money has a worse character while I'm arguing they just had greater opportunity.