Catch 22

I read these books as a kid: A series of unfortunate events

Slaughterhouse-Five

My journal

Probably a little different than what you're describing but I'm reading blood meridian right now and it's very good. It's about a 14-year-old runaway in 1850s America where everything is fucked. He gets in increasingly desperate and violent situations to try and survive

Great Expectations

Take a look at the works of David Sedaris. Those fit the description, and are funny.

Like Wind Against Rock by Nancy Kim

Model Home by Rivers Solomon

The Book of Dead Birds by Gayle Brandeis

Sisters One, Two, Three by Nancy Star

Some Kind of Happiness by Claire Legrand

A wolf at the table

I was surprised how heart wrenching Upton Sinclair’s The Jungle was. Growing up I heard it was about meatpacking plants in Chicago. Technically correct, but very much a tale of things not going well. Enjoyed the journey despite the sadness!

I haven't read This is Where I Leave, so don't know how similar it is, but I really liked Demon Copperhead & it fits your criteria - trials and hardship but with some humor.

Once Were Warriors

Once Were Warriors is Alan Duff's harrowing vision of his country's indigenous people two hundred years after the English conquest. In prose that is both raw and compelling, it tells the story of Beth Heke, a Maori woman struggling to keep her family from falling apart, despite the squalor and violence of the housing projects in which they live. Conveying both the rich textures of Maori tradition and the wounds left by its absence, Once Were Warriors is a masterpiece of unblinking realism, irresistible energy, and great sorrow.

Dysfunction, alcoholism, domestic violence.

But it's not funny, sorry OP.

Job

The Death of Bunny Munro

Appearantly they are doing a tv series based on the book now.

Naive Super

The Corrections by Jonathan Franzen features a pretty dysfunctional family and has some funny bits.

Infinite Jest by David Foster Wallace is probably one of my favorite novels and has both a dysfunctional family and characters living in a halfway house. It's main motif is addiction, be it to entertainment or substance. However, at a over 1000 pages and with a non-linear plot, it might require some persistence to get through.