Gi(a)rlish Number, Imouto sae Ireba Ii. Recommendations
Occasionally sentimental comedies revolving around anime, manga, and light novels as a profession. Many aspects of the industry are explored thoroughly, such as "generic" light novels and their adaptations still being born from a place of passion for the medium, and what it takes to go from being a consumer to a creator.
Self aware shows that enjoy taking jabs at the industries they are set in, both revolving around a protagonist with some unlikable qualities.