In 19th century British usage, a remittance man is an emigrant, often to a British colony, supported or assisted by payment of money from his paternal home. As a general term remittance man or remittance woman could mean anyone living away from home supported mainly by their family in a different house, neighborhood, city, or country regardless of their reason for being there. Such a person may be seeking business fortune, education, extended vacation, a new place for the family to move, employment, or safety from personal, family, or legal troubles.
Note that in this context, money is being sent in the opposite direction to today's usual usage of the term remittance, which means money that migrants send back into their home countries.
Successful remittance men
A remittance man could be a younger son trying to escape the shadow of elder dominating sons to seek his own fortune and proof of worth, such as George Vanderbilt of the Biltmore Estate. Other less famous persons who lived off family remittance payments came from middle-class families who could afford to send them. These might move from their east coast family home to the west coast seeking fortune and starting new businesses as American commerce historically expanded west.
Dark-side remittance men
Within Victorian British culture, this often meant the black sheep of an upper or middle-class family who was sent away (from the United Kingdom to the Empire), and paid to stay away. These men were generally of dissolute or drunken character, and may have been sent overseas after one or more disgraces at home. "Remittance men" also lived in several towns in the American  and Canadian West  There were also 'remittance women' but they are rarely discussed in scholarly works. Many remittance men were sent to the Australian Colonies.
American writer Mark Twain and Canadian poet Robert Service make references to those specific "remittance men" in some of their literary works. The term was in casual use in Alaska until the late 20th century, usually with a derogatory intent. Judith Wright (1915 -2000) wrote poetry on the remittance man.
In past commercial mass entertainment novels the dark side remittance man has been popularized. An example of this usage is in Robert Louis Stevenson's book The Wrecker where the character Tommy Hadden is cast as the 'remittance man'. In the book
|“||Tom Hadden (known to the bulk of Sydney folk as Tommy) was heir to a considerable property, which a prophetic father had placed in the hands of rigorous trustees. The income supported Mr. Hadden in splendour for about three months out of twelve; the rest of the year he passed in retreat among the islands.||”|
- Watson, Roderick (2007). "‘"The unrest and movement of our century": the universe of The Wrecker". The Journal of Stevenson Studies 4.