(including things we would consider ourselves in the First World much too good for, like working for organized crime syndicates) to move up beyond that income bracket.

That's actually a fun statement!

1) Many people getting this far in this thread will be surprised to learn the the First World does not have organized crime!

2) it is widely stated that the source of a disproportionate number of criminals in our society are unemployed "lower class" youth, where for these purposes if is sufficient to read "lower class" as meaning hard-to-employ.

You need to account for the cost of living in the US, especially the cost of housing, since one can be arrested for not having any.

THere are a bunch of homeless people in Sandy Eggo (where I live) that manage to evade police. Are you SURE being homeless is a crime?