Is it not?
1. Having something comes with the risk of loosing it.
2. with risks comes the potential to add worry.
3. People with more to lose have more potential to be worried about it
How is my reasoning flawed?
The only thing you cannot lose is your past. You might lose the memory of it, but that does not nullify it's existence.
2. Again - the ability to take risks increases - this is one reason the rich get richer - they can make riskier investments while the poor can't make such bets
3. People with more to lose - are the people who lose a greater percentage of their savings - a rich person losing $1000 vs a poor person losing $1000 - a poor person loses more
Logical reasoning works best with absolutes, things like individual motives (applied to larger populations) and "risk", "worry" etc have a lot of nuances - you need to work with probabilities backed by data.