4. In a larger and more general context, a Trustafarian is someone who lives off of a trust-fund or off of rental income from property that he/she inherited. In previous centuries certain rich kids received stipends or allowences from their parents to live a cultured life (usually before settling down while looking for a suitable spouse, and later getting a sinecure in the family business) without actually working for it, those could be now called proto-trustafarians. Anyone who livess off of income he/she hasn't actually earned and keeps it quiet is a Trustafarian, who may in fact be, and often is a decendant of proto-trustifarians.
John's not only a trustifarian, he comes from a long line of proto-trustifarians, in the last 100 years the family has worked for maybe a year.