This is what I think is going on: in a case like this, there's probably no actual crime (as defined by law), because investing is inherently risky, and therefore losing money is normal. You, as a scientific-minded individual with a basic knowledge of economy, will only convict the adviser if there's actual proof of mismanagement. I'd bet that, in the average case, it would be rather hard for a typical 60 y.o. woman to get evidence of that (assuming there is such a thing). If you said "yes" to the "too many frivolous suits" question, you would be easily conviced that the woman has no real argument, but is suing anyway.
Also, from the "do you like crosswords" question, if you say "no" you get this:
> This is a question about your cognitive style. The plaintiff lawyer believes you may be more likely to respond to the plaintiff's more emotional theme of victimhood rather than looking deeply at the legal and financial details.
I read that as "we don't really have a case, but if our jury identifies with the old woman, they may rule in her favor out of compassion".