Perhaps I'm looking in the wrong direction by asking about first day of school books which depict school as something to look forward to rather than to fear. As you say about community involvement in your post about The Concrete Lorry, maybe the idea that school is a positive thing is best absorbed through a good story.
Two good school stories we've been rereading lately come from authors we've written about regularly: Peggy Rathmann (Good Night, Gorilla; 10 Minutes Till Bedtime), and Kevin Henkes (Julius, the Baby of the World, Kitten's First Full Moon, A Good Day).
From Rathmann: Ruby the Copycat. Ruby is a new girl in Miss Hart's class, with Rathmann's trademark fuzzy hair and lit-up face (see the unspecifically gendered child in 10 Minutes Till Bedtime. Or the gorilla.).
The book covers Ruby's first week of class. She's seated behind Angela, "the girl with the pretty red bow in her hair," and is so entranced by her that Ruby can't help but copy everything Angela does: she goes home for lunch and returns with a bow in her own hair, tells the class that she, too, was just flower girl at her sister's wedding, and essentially plagiarizes a poem that Angela writes. Angela is at first flattered, but becomes increasingly upset by Ruby's attention. Miss Hart gently intervenes, and after a little backsliding, Ruby is encouraged to claim her own interests and act like herself. School is the social environment where all of this plays out, and the influence of peers is clear. Miss Hart is a warm and accepting presence, who ultimately helps Ruby shine in the eyes of her classmates. Eleanor is very much into the social dynamics of the story, and Isabel loves to point out the pictures of cats on the wall.
From Henkes: Lilly's Purple Plastic Purse. We've mentioned Lilly before, but have not yet given this book its due. Lilly, who appears in several other books as well, is a confident, outspoken, dramatic child (well, mouse). She begins this story in deep adoration of her teacher, Mr. Slinger, who does seem pretty cool:
Mr. Slinger was as sharp as a tack.
He wore artistic shirts.
He wore glasses on a chain around his neack.
And he wore a different colored tie for each day of the week.
Instead of "Greetings, students"
or "Good morning, pupils,"
Mr. Slinger winked and said, "Howdy!"
For a while, inspired by his coolness and the rainbow-striped shirt Mr. Slinger wears in one illustration, I thought Henkes was subtly indicating that Lilly's favorite teacher is gay. I was wrong: in Lilly's Big Day, he marries a female teacher at the school, and Lilly lobbies hard to be their flower girl. (I'll admit, I was a little disappointed.)
Lilly gets a new, awesome purple plastic purse, shiny jingly quarters, and sparkly sunglasses one weekend, and brings them in to school to show off. She can't keep quiet about them, and Mr. Slinger confiscates them until the end of the day. Lilly is furious, and draws a mean picture of Mr. Slinger, sneaking it into his bag at the end of the day. Of course, he leaves her a very sweet note in her returned purse, and she feels TERRIBLE. This is why it's a good book to help discuss guilt over doing something which hurts someone else's feelings. Lilly apologizes, and draws a new picture. Her mom writes Mr. Slinger a letter, and her dad bakes cheese balls to bring in. All is forgiven, but the feelings are deeply felt.
School here is exciting, social, and full of learning. It's Lilly's main focus throughout the book: the first sentence is "Lilly loved school." All the adults, teacher and parents, are understanding but firm -- no one makes excuses for Lilly, and they help her make amends. Henkes also has a nice comic-book-like way of drawing some of the pages, with multiple images and lots of little throwaway dialogue lines or captions in the pictures. It's a fun book to peruse -- way too long for Isabel to sit through at the moment, but one of Eleanor's favorites.
So it's back to school for us all!