Earlier quoted context omitted.
The reason that $1000 at 90% odds and $900 at 100% odds are used in this example is the expected value is the same in both cases, making the situations 'equivalent'. A 90% chance of losing $9000 has an expected value of -$8100.
The way I read it is this: Do you want to be guaranteed you'll lose $900? Or do you want a 10% chance you'll lose nothing at all, with a 90% chance you'll lose another $100? So given a choice between being (nearly) totally wiped out, or having the chance of not being wiped out, people take the chance of keeping their cash. Makes sense to me.
I also agree that the reasoning changes a lot if this is a one-time event vs. a regular occurance.