It's the First Day of School...Forever! - R.L. Stine

It's Artie's first day of school.  Between the syrup in his hair, his dog attacking the principal, losing a priceless scorpion, making enemies of the most popular kid in school, and having to navigate a totally creepy basement, it isn't a great day.  Then he goes to bed.  And wakes up to begin the first day of school.  This time he tries to do things differently, but it doesn't improve his situation.  Things get weirder and creepier with each first day of school.  Just when you're ready to call in the SWAT team to help this kid out you make it to the last chapter and realize....well, you'd have to read the book to know that!  R.L. Stine does what he does best with laughs and chills and tosses in a Twilight Zone worthy twist at the end.