I finished the game with little trouble. It's an extremely long game, but FWIW, I recall very little running "back and forth" between towns being necessary. Maybe once or twice in the whole game, tops. If you can't get past the area you're in, chances are you haven't talked to the right character enough times. Also, stay at the INN in every town as some story-progressing events only trigger at night.
I stayed at the inn in the 2nd town and it didn't go to a night scene, so I assumed the inn only healed you. I know I stayed in the inn in the 3rd town as well and no night happened. Does night only trigger if the conditions are special? I never use heal herbs actually, I always sleep in the inn.
Yeah, you'll wake up in the middle of the night after hearing some sound outside or somesuch as opposed to just waking up in the morning. Obviously this doesn't happen in every town, only some, but I can't remember which because there are so many, so I just say try it in all, especially if you get stuck
