Loud hint warning.

Hmmm

Let's add another title and give #33 another shot:

#33: The Errant Errand
Fight for Your Time Slot!
That's Just Frank
The 6th Cutest Girl
A Terrible Monster Appears!

#32: Muhahaha! You think you outsmarted me, the mighty Moldorc?! I don't think so Yoked Girth!
...so stop by, fill up, and make sure you get your Billy Hog hot dog before you jet away.
Introducing Apricop... it's a punch to the gut!
Good morning Brookhollow. Today is October 20, 1990.

#31: guessed by coolbeans: Romance of the Three Kingdoms XIV

#30: Your heroes grow old and retire - if they aren't killed on the battlefield.
They also can acquire strange body parts, like a fire arm, a wolf's head or crow's feet.
The mages can manipulate objects in the battle stage to do damage.

#29: Draw the map of the high school yourself on graph paper.

_{ranking in the guessing game, list so far}

Haven't done some clues for a few days

#39 - correctly guessed - Crash Bandicoot 2
- More forgiving than its predecessor when you’re trying to collect those precious jewels.
- Bouncing on your buddy’s head will net you some extra lives.

#38 (incorrect guesses - Castlevania: Symphony of the Night, Bloodstained: Ritual of the Night)
- A game that was retconned by the man who was heavily involved in introducing the gameplay model it uses... so much so that many of the games in this series with this style are commonly referred to using a portmanteau that has part of his name, and part of the series the games are from.
- In addition to the standard game, there are four different modes that can be unlocked, each of which will change the way you approach the game.

#36
- Do you want to go hiking or mountain climbing?

#35
- If you rest long enough in a certain place on that train ride, you will get a nasty surprise.

#34
- The guy who dies shortly after you arrive on location shares his name with a guy who suffers a similar fate in a movie franchise that no doubt influenced this game.

#33
- Smelling of urine isn’t necessarily a bad thing.

32
- That damned doctor can make or break a run for a frustrating unlockable.

My list so far

Adding possibly the final hints to these two titles:

35) This game has several clips of live action footage, including one that creeped me out despite being very mundane
Hint 2: You could call it Conspiracy Theory: The Game
Hint 3: But what does S3 really stand for?

34) The protagonist of the first game is really old in this second entry, but in the third game he's young again.
Hint 2: But this game has a different protagonist who shares his name with a letter from the greek alphabet
Hint 3: Visual novel meets puzzle game

Maybe Crash Bandicoot 2? Though don't know about that second hint...

That's correct. Unlike the first Crash, you don't need to get all the boxes in each level without dying to get the gems (which you obviously got). For the second hint, the small polar bear you ride in some of the levels is in one of the rooms in the hub. If you bounce on its head you'll get some extra lives.

Some more hints.

34 - Though not every faction will be affected as harshly, when the hordes from the steppe arrive, you better be prepared.
Hint 2: An attack from hordes like this happens twice in the game, once from the northeast and once from the southeast. These attacks come from factions that are unplayable.
Hint 3: There is a third unplayable secret faction, but you'll not always be able to meet them, because you'll need to travel to the new world.

33 - Three influential families and the central government, allies at first, until one seeks to rule them all.
Hint 2: This technically happened in real life too, where the leader of one of these families (they're represented in the game) had cast the die.
Hint 3: So while this game takes place during the start of the empire, its expansion leads up the very end of it (or, what was the end in real-life anyway).

32 - There's a strange bug in the steering in this game where if you make a couple quick, short turns in succession you'll be stuck with a long, big and wide turn that'll send you all across the stadium.
Hint 2: This means you can really annoy your friends when you create a track with a couple of short corners in a row and then a table top, in the map-editor.
Hint 3: Speaking of the map-editor, I've always found it too bad that you could only make tracks for the stadium mode, and not the country modes.

31 - In real life, getting cockroaches in your hotel room would be bad, but here, it's completely doomed and you'll need to demolish the rooms and rebuild them.
Hint 2: To prevent this, you'll need to also build cleaning centres, which are as big as two single rooms plus a double room, and connect them with service elevators.

30 - Shouldn't rock the boat because someone will puke.
Hint 2: Because you'll really make him sea-sick. Guessed by Darashiva - Warcraft II: Tides of Darkness

30: Warcraft II?