WI if bums became as fashionable as gypsies?

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WI homelessness became fashionable?
TV shows would follow: “Vagabonds of Vancouver,” “Bottle-Collectors of Boston,” “Homeless of Houston,” “Crack-Heads of Calgary,” “Denver’s Dumpster-Divers,” “Meth-Heads of Maple Ridge,” etc.
TV cameramen would follow the homeless doing their nightly rounds of nasty neighbourhoods, flea-infested flop-houses, opium dens, slum land-lords, Soup kitchens, etc.
Yuppies and hipsters and metro-sexual lumberjacks pay big bucks to “slum” a night in a dark, dingy alley, etc. They pay double for greasy, frayed and filthy trench coats and blown-out shoes, etc. Te most fashionable shoes are bought directly from winos. Metro-sexuals brag about offering a hobo a hundred dollars and a new pair of shoes to replace the “holy” pair, then they “treat” the homeless guy to a new pair of shoes at Discount Shoe House. They broadcast the transaction on their cell-phones, Facebook, instagram, snap-chat, etc.
Cardboard cabins are sold at Pier One, Urban Barn, etc.
 
I... don't think Roma people have ever been fashionable, more like "romanticized". And, even then, that romanticism is mostly a result of very few people of that ethnicity reaching American shores, and even fewer deciding to keep being "children of the wind" once they got there, to the point that a few Americans don't realize they're real (see: White Wolf's very unfortunate supplemento about Old World of Darkness, featuring curse-slinging Romani fortune tellers duking it out with werewolves and vampires and others... and hunted like them by the Hunters of the supernatural).

The only way I can see what you think of happening is making so that "being like a gypsy" could be percieved as the next best thing as "being a Hinduist Indian" for Indiophiles. And even then that requires tons of hoop jumping.
 
The tramp, a long-term homeless person who travels from place to place as a vagrant, was kind of romanticized by Chaplin's character.

The Irish Travelers also have been romanticized?

Also agreed that gypsies have never been fashionable. They are kind of lumped into the "oriental exoticism" that is based on myth rather than fact
 
Re-reading the OP a bit more carefully, it looks like to me that he's trying to ask something more along the lines of "WI there were Mondo [exploitative and crude] documentaries of homeless camps and skid rows?", since what he's referencing are a thing in some places (especially Europe).

To which I can only answer that there would be a fairly higher dislike of the homeless, since Mondo movies about Romas often have moved an ambigous relationships between the majority and Romas (one rife with conflict I might add) into the territory of costant open hostility and permanent antiziganism, due to their heavy focus on the criminal elements and the degraded lifestyle they often conduct.
 
This just feels in poor taste. Traveller folk find themselves facing a lot of bigotry and hatred up to and including neonazis murdering Roma minorites in Hungary and the ruling party in the UK including in its campaign literature assurances that they'll confiscate the homes and property of Travellers. People who are homeless die in the cold and wet often forced into their circumstances through poor luck or mental health. "Metrosexual" is a dumb phrase with homophobic, sexist connotations and all.
 
... I'm somewhat "amazed" that you seem to lack such a format in anglo(?)-american TV. Seems at least with this - tasteless reality-shows - we have an edge in Germansy :
  • "Armes Deutschland" ('Poor Germany')
  • "Harzt und herzlich" ('Harzt [lowest form of social support] and heartly')
  • "Ein Koffer voll Geld" ( 'a suitcase of money' ... given to some people on the lower/lowest end of societly esp. regarding money)
  • "Der Kiosk" ('the Kiosk' in many german cities kinda 'meeting' point for homeles to get their alcohol)
  • a reality'show' about drug addicts living on the street [focused mainly on its 'older' personnel) I've forgotten its name
These are daily soaps romanticising the living of these people on and below the bottom of society
 
WI homelessness became fashionable?

You mean what if there were lots of songs about hoboes. with titles like "Hallelujah, I'm a Bum" and "The Big Rock Candy Mountain"? What if there were a milieu--let's call it "Hobohemia"--where 'hoboes, intellectuals, artists and radicals" mingled? https://books.google.com/books?id=OsGMuyFE_FQC&pg=PA101 What if there were a whole labor union--let's call it the "Industrial Workers of the World"--which devoted special effort to organizing hoboes? Hint: all these things happened!

But, you might say, all that was long ago. What about more recent times? Well,....

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Trailers for sale or rent, rooms to let, fifty cents
No phone, no pool, no pets, I ain't got no cigarettes
Ah, but, two hours of pushin' broom
Buys an eight by twelve four-bit room
I'm a man of means by no means, king of the road
 
First off: my apologies to European Romas. have only seen a few at Spanish tourist traps. Spanish citizens were harsh on gypsies, warning us that they were all pick-pockets.
I was referring to the more romantic films, , sings, etc. of North American hobos during the 1930s. Hobo lifestyle was romanticized by singers like: Woody Guthry, U.Utah Phillips, etc.
This thread was also based on my personal experience living in a VW van, dumpster diving, visiting the food bank, driving buses full of homeless through Vancouver’s poorest neighbourhoods, wondering why their were so any drug addicts in Maple Ridge, B.C. and Perris Valley, California.
 
They aren't commonplace in the US, which is where the OP is from.

Close!
I am from Canada, but have also lived in Germany and the USA.
Gypsies/Roma are rare in North America. NA gypsies do not dress or travel in distinctive clothing or vehicles.
One friend is descended from Irish Peaky Blinders, but is only distinguishable by her Irish accent.

OTOH I do live near Vancouver, which has the mildest climate in Canada, so poor people migrate here. Because Vancouver is also a port city, it is a major channel for drugs entering NA, so we have more than our share of drug addicts. These poor people tend to congregate in Vancouver’s Downtown East Side (centered on the corner of Hastings and Main). Fortunately, dozens of charities feed them above the starvation level.
 
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According to Wikipedia, only about 1 million gypsies live in the USA and a mere 3,800 live in Canada.
Roma culture was disrupted when many of them and across as slaves (USA) or prisoners (Australia).
 
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