The game didn't really give me any trouble at all up until the Quadrangle, then it started getting difficult (which is the reason I play puzzle games). By the end, I was definitely tearing my hair out when beating every stage from the start without dying. It was exactly what I was hoping for.
Getting gold on a level will allow you to skip it in subsequent playthroughs, allowing you to beat the game much more quickly when trying to see all 8 (!!!) endings. Thank God for this feature.
Character interactions are dull in the beginning, especially if you don't make a point to listen for when people come in and out of the bar. Pretty much every characterized sheep from the landings shows up in the bar every night, you just need to look for them because they are easy to miss. Their stories become pretty interesting and deep, especially those of your close friends (and the only way to decipher some of their cryptic babble is to see a particular ending). I made the mistake of only really befriending one person at the bar in my first playthrough, and I was left confused by a lot of the interwoven threads between some of the characters. Befriending everyone in subsequent playthroughs made the game make a lot more sense and more enjoyable.