G'day Bill,I have always described a Colonial Experience Man as a Remittance Man with a job title and an option on a return ticket.
The late 19th century sense of Jackeroo was pretty similar, before it lapsed into meaning no more than a 'stockman'. Interestingly, its early 19th century sense was of any white man living beyond the Government's "Boundary of Settlemnet" ... essentially a 'squatter' in the earlier senses. Presumably, both terms went up in the world as the 'squatted' properties were legitimised and made money.
Regards,
Bob Bolton