Homelessness in Dramaland

One of the protagonists (Takeshi) is homeless and agrees to be the other protagonist's (Sumire) pet so he can live with her. 

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The FL starts off the story without a home and ends up moving in with a bunch of yokais out of desperation. She is homeless for a very short amount of time.

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The leads both experience homelessness in the beginning of the story

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One of the leads has sex with people as a form of payment for housing. 

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Chihiro is chronically(?) homeless until he moves in with Haoren, who has an unstable home life (keeps needing to move into somewhere else)

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Hiromi gets kicked out of his girlfriend's place and ends up sleeping in his car. With nowhere in particular to go and no job in sight, he travels to find the sea. Finally, he ends up finding room and work at a bed and breakfast 

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• Silly

The ML pretends to be a homeless beggar in the beginning of the story. There is also the beggar guild, which seems to be made up of people without homes. 

(Please note: the Beggar Guild is a wuxia trope of the jianghu setting. Beggar Guilds can be found in many different stories including the OG Demi-gods and the Semi-Devils, though the extent of homelessness within the guild is not always clear or consistent across its many representations in dramaland)

The lead loses his family and ends up homeless (iirc) before getting taken in by a peking opera troupe in the beginning of the story. 

There is a supporting character who is without a home. Chihiro takes him into her home, but he does not stay long. Eventually he ends up squatting in an abandoned building before passing away. 

The second lead is between homes, often staying over with someone he knows instead of having his own stable place to live. By the end of the show he has moved to another town to further his education but the state of his housing isn't explained. 

The FL spends a few episodes being homeless after she runs away from her abusive relationship with her husband and in-laws. She flees to a city and ends up squatting a run-down house while trying to find work as an undocumented person. This is very difficult and she ends up in a predatory work environment because of it. Eventually, she gets someone to forge documents for her and establishes her own business. Once she's saved up enough money, she buys a plot of land, and eventually a shop. 

• Survivalist
• Hard worker
• Fleeing bad home life

While one of the leads does have an apartment he belongs to, the home he lives in is unsafe and he often ends up sleeping in parks to avoid being abused. He also sometimes sleeps over at his friends place for the same reason. 

• Fleeing bad home life

One mysterious and silly character is a homeless beggar. SPOILERS: this character is very powerful despite her appearances. She is homeless throughout the duration of the show. 

• Mysterious
• Magical
• Silly
• Gives guidance

A supporting character is homeless for the full duration of the show. He is mysterious and knowledgeable with hidden secrets

• Mysterious
• Magical
• Silly
• Gives guidance

Miki (one of the leads) starts off the story poor and when asked where he sleeps he says, "wherever," before crashing with one of the other leads and living with him for most of the rest of the movie. 

• Rough
• Quick to take advantage of an opportunity

This is a special of the main show, Ikebukuro West Gate Park. In this special, the protagonist becomes homeless after his home is suddenly sold to loan sharks. As a result he sleeps in a truck where his mom's fruit shop temporarily lives in, and his mom stays in a sauna (which is cheap and some let you stay overnight). Meanwhile, Makoto eventually is sought out by a homelessman selling manga, asking for help knowing that Makoto has sleuthing abilities. Recently, the homeless have been preyed on by a mysterious duo who drugs, lubes, and then crushes body parts of the homeless (no homeless people die in this). We also learn that amongst the homeless is Makoto's dad, who lives in a swanky make-shift home of plastic and miscellaneous things. Makoto ends up in one of these luxury make-shift homes too. The special episode is basically a call to stop violence against the homeless. By the end Makoto and his mom are housed, and Makoto's dad is working though its unclear where he lives now. The other homeless cast also have unknown outcomes in terms of their housing. 

i mean... just read the synopsis

The lead's parents both end up homeless at different points. The mother is homeless almost the entire time as a criminal on the run. Her father is homeless actually almost the entire time too now that I think about it, after being kicked out by his ex-wife. There's also a song made by one of the protagonists about homelessness. And one of the protagonists is homeless in the beginning of the show and lives out of his car. They all end up housed by the end.