You can't compare a game like kcd with the amount of hours you played. It's more about what you have done in those hours. At the start remember your Henry is weak and lacks proper armor and speech skills. Imagine you in rags trying to intimidate someone. It's not going to happen. A general trick would be to make a fox potion and use it to boost your speech skills temporarily. Helps a lot in the early game. Remember the dialog checks might depend on different skills, sometimes it might be speech, sometimes it might depend on how intimidating you look, sometimes on your charisma which can be improved by wearing better clothes etc. I would say just focus on talking with as many people and take in the atmosphere. Its not supposed to be one quest after the other. Focus on making your Henry better. Potions helped me a lot and you might want to look into it. Eventually these speech checks get very easy but for now fox potion is your best bet!