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Hi! I'm going through a pretty tough time in my life right now, so I'd like to ask you to recommend me some movies and doramas where characters (neet and hikimori, but not necessarily) struggle with financial anc social problems and insecurity to change their lives, find a job, and socialize. Bonus points if they show basic work and teach the importance of working and providing for yourself. Of course, it would be better if it were a dramedy or comedy, possibly black comedy, but with a useful motivation to find your way in life, like in GTO or Dragonzakura.

In general, motivational (near) comedy shows about how young adult characters struggle with problems to become full-fledged members of society.

Freeter, Ie o Kau - Exactly like your description but it's a bit serious and stressful at times.

The Man of 0.5 - Breaking social phobia but it's too short with only 5 episodes. It's fun and sweet family focused drama.

Dating: What's It Like To Be In Love? - It's romance with a spice of comedy but ML is Neet. He is a bit like the ML from "If Talking Paid" who is masterful in rationalizing his weakness. Very fun drama (I liked this more than "if talking paid") but you need to endure the weird 1st episode.

The Birthday Mystery - It's a Neet Female drama. However it's romance and I do not remember what was motivating FL to get out of the neet zone. Either the love or different thing. But it was a good drama with unpredictable plot development (not unpredictable twist though).

RobertBobert:
In general, motivational (near) comedy shows about how young adult characters struggle with problems to become full-fledged members of society.

If you want struggling young adults drama with focus on work that's motivating to watch without they being Neet or Hikikomori:

Boku no Aruku Michi - Autism ML (non genius) adapting into society and work and be independent from family. Less comedy but very inspiring with some focus on work.

Sleepeeer Hit! - We will see the struggle of people (side characters) from the POV of FL which is the protagonist. Very inspiring drama that focus on manga publishing. You will also learn a lot about Japanese manga industries.

Passion for Punchlines - Based on real life story of two Japanese comedians struggling to get recognition from public. The drama looked weird at first because it's split into two stories of two people that wasn't connected until in later episodes.

Kiseki no Hito - It's a rendition of "Miracle Worker" but this time the ML protagonist is unemployed and unmotivated (and stupid) until he meets the "Helen Keller" of this story. Very funny and motivational at the same time. No professional work but it's about finding purpose in life.

Uta no Oniisan - Musician ML split from band so now reluctantly has to work for Kids TV Show (due to some circumstances). He hated it at first but later will find motivation and the meaning of being serious in what you do. Yeah it's sounded cliche but still a good one.

Kazoku no Uta - Once a popular musician now has been struggling to make end meets. To make things worst his illegitimate daughters come to live with him all of sudden. It's a nice family drama with stubborn ML's dilemma in either being himself or become poor.

Maybe...

Marry Me! - FL has severe social phobia, she doesn't get a job but her world opens up

The Romance Manga Artist - ML has social phobia

How to Find Happiness - FL undergoes a change

Overprotected Kahoko is the opposite of dark comedy, but it has a FL who faces great change from being coddled and protected into becoming an independent woman. It's sweet.

Romantics Anonymous features two people with anxiety disorders. I liked that the drama didn't throw a switch to "cure" everyone. People with mental issues aren't often healed instantly; it can take years or be a lifetime endeavor. It was gratifying to see the ML and FL learn how to cope and live more successfully even while struggling with their afflictions.

I enjoyed both the above. Each was life-affirming in its own way.