The Books
Max Shulman apparently wrote two books' worth of Dobie Gillis short stories, the first one being of course The Many Loves of Dobie Gillis, and the second (published to coincide with the show's premiere) called I Was a Teenage Dwarf.
The first one is available on Amazon in various forms, including Kindle ($2). I've begun reading it, and will list the similarities and the differences below, as I go along:
Similarities:
Dobie is a teenage student, being supported (though not in the style he'd like) by his father.
He's crazy about girls.
Both Thalia Menninger and a Zelda-like character appear in the fourth story, "The Sugar Bowl."
Differences:
Most glaringly, so far there's no Maynard.
Dobie is enrolled at the University of Minnesota, rather than being in high-school at first.
I'll post more as I read further.