These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Family-Unfriendly Aesop: Most stories go the "Never give up! With enough hard work and dedication, you'll achieve your dream!" route. This one doesn't. The moral of the story is that sometimes, hard work and dedication to a dream is just bashing your head against a wall, and the harder you work toward something impossible the more miserable you'll make yourself. Sometimes, you have to give up on one dream... so that you don't give up on living altogether.
In fact, trying to use the "Don't give up" speech causes D to fly into a rage and stab you. And then he gets killed by the Crooked Man.
It can be argued, though, that the point was closer to "Don't blindly follow your dreams, and have a fallback plan" rather than simply give it up, since he (accurately) points out that continuing down a crooked and broken path in a blind pursuit of your dreams can cost you more than you gain. He also tells him he should try the Bar exam again, but to consider other options as well. Plus no one ever said your passion can't be just a hobby any ways.
Also: forgetting about a lost connection with someone isn't progress, it's a coping mechanism. Sure it's healthy to "move on", but ignoring all the good and bad times you had with someone is doing yourself a disservice. You are cutting out a very important part of your life and history and suppressing it. It may be painful to remember because it brings about that "I wish I still had that" feeling, but you don't learn anything from the past if you pretend it never happened.
The lesson from Fluffy is more obscure, though. It can be argued that the lesson is supposed to be "parents are just dicks sometimes and there's nothing you can do about it". On the other hand, Fluffy waited for someone else his mom to solve his problems for him when he had plenty of opportunities to fix it himself he's lost so why not go down the street to the police station and ask for help? Then it can be argued that the lesson is that just because someone doesn't help you his mom, again, doesn't mean that they don't care about you. It may just be that they don't know you need help or are somehow unable to help. Finally the lesson could be "don't act brave". Facing your fears is fine and all, but if you get lost and wander around for hours and hours on end refusing help at every turn, you are just going to make things worse. For example, hunters that get lost in the woods (in groups of 2 or more, usually) often can't find their way out and they start making foolish decisions out of pride. When they are found, it is common for them to claim that they never got lost. Another example is when this troper got lost in the woods as a kid. I found my way out of the woods where people were several times, but I was too embarrassed and fearful to ask for help. Refusing assistance or refusing to acknowledge assistance isn't putting on a brave face, it's ignoring the facts. Whether it's for the sake of pride, out of embarrassment, fear, or just born out of plan stubbornness, refusing help when you clearly need it is just not a good idea.
In the second fight, you can hit the Crooked Man through a table, so all you need is get him trapped on the other side of a table and start swinging until he's dead.
Harsher in Hindsight: Later on in the game, you find out that Paul has the ability to see and sense the paranormal. He knew from the beginning that something was off about the room, but didn't mention it to David and let him move in there anyway, which directly led to all the events of the game.
Insane Troll Logic: Uri's games have a general trend of forcing you to choose the LEAST realistic option during a choice scene in order to get the best ending. In The Crooked Man, you attack people on the brink of committing suicide, tell people to give up on their dreams, and tell people that it's bad to let go of the past. Realistically, none of these would give a good response. Justified for this game in that you are dealing with the ghost of a person who simply wants to be told the hard truth, and a malicious spirit that will not listen to reason.
Jerkass Woobie: D. He's got an incredibly rude and snobby personality, but we learn over time that he's become that way because he's been trying and failing for years to become a lawer, something he's wanted to do since he was a boy, and has received nothing but mockery and scorn for it. The fact that he softens up eventually definitely helps. If you get his bad ending, however, stabbing David in a fit of frustration and despair kind of loses him this title.
Nausea Fuel: The dead cat, the Crooked Man eating a model of an embryo (it was fake, but still), the Crooked Man's impossibly cricked neck...
That One Boss: The dodgy fighting mechanics are difficult to use due to the fact you need to stop moving in order to hit The Crooked Man, while all The Crooked Man needs to do is touch you to hurt you.
Paranoia Fuel: It is heavily implied by certain elements of the game that although the Crooked Man "locked onto" Duke and David, it wasn't actually created by them. It, or other beings like it, exist independently waiting for people susceptible to its influence that it can drive to suicide or kill.