Full Disclosure: I have an entry in the Jam.
Spirit and essence of Harold: Harold is the most Harold he can be
Fun: Interesting game
Creativity: Unique idea to build a game within the game. This could be built upon to create tutorials. Glad to see someone else incorporating Text-To-Speech for narration.
General Comments: A couple of typos and grammatical errors but otherwise well-crafted. It wasn't quite clear what happened the first time the game looped. Maybe add a comment in the first time loop about going back in time or being given another chance.