Thanks for playing and for your feedback! ^^
As for the visuals, they're intentionally inconsistent (at least between the characters and the environment), because it was meant to show a sort of collision between two worlds (the one Fletch is from and the poolrooms-esque location), but we didn't make it clear enough or emphasized it enough due to a lack of time. >.>
Rests are randomized, so getting a long string of them is nice! ^^ But this game does make basic enemies harder for every encounter you've done so far, so they do make the fights after rests trivialized before a difficulty spike at the boss. As for the game over screen, sadly we didn't implement that in time. :(
The orange shield is meant to represent magic armor, which blocks magic damage. Definitely should add a way to clarify that and other icons in the future.