Here are some more clues:

32.  This game is the first time that this series had a female as the main protagonist.  However, some fans consider this game to have no "main" protagonist since several characters get a lot of attention from the story.

31.  In this entry you have amazing control over the character's main weapon as you fight your way through the home of the greatest villain ever.

30.  There is a PS4 first party exclusive that is strongly inspired by this third party entry, the first time this franchise went open world.

29.  This first entry in the series is based on a classic piece of literature.

Here are some more clues:

32.  This game is the first time that this series had a female as the main protagonist.  However, some fans consider this game to have no "main" protagonist since several characters get a lot of attention from the story.

31.  In this entry you have amazing control over the character's main weapon as you fight your way through the home of the greatest villain ever.

30.  There is a PS4 first party exclusive that is strongly inspired by this third party entry, the first time this franchise went open world.

29.  This first entry in the series is based on a classic piece of literature.

Here are some more clues:

32.  This game is the first time that this series had a female as the main protagonist.  However, some fans consider this game to have no "main" protagonist since several characters get a lot of attention from the story.

31.  In this entry you have amazing control over the character's main weapon as you fight your way through the home of the greatest villain ever.

30.  There is a PS4 first party exclusive that is strongly inspired by this third party entry, the first time this franchise went open world.

29.  This first entry in the series is based on a classic piece of literature.

#38: A PC-exclusive Pinball game with a horror theme.

Hint #1: Tables are a haunted Castle, a Dungeon, and Frankenstein's Laboratory, complete with the Monster in it's center.

Hint #2: It's the second game in that specific series, 3 more were to follow.

Hint#3: The predecessor had 3 tables in space, with buildings from Outpost, the successor had Dinosaurs, the next one had a NASCAR theme and the final one a rollercoaster theme.

Hint #4: They also made a Minigolf game with an identical naming scheme, just switching out the Pinball at the end for Minigolf.

Hint #5: The series was published by Sierra On-line

Looks like nobody found out about this one either, which is a bummer. I still find that 3-D Ultra Pinball: Creep Night is the purely digital best pinball game ever made, and that's sad since it uses a 16-bit executable to launch, meaning it doesn't work on 64-bit OS anymore unless you virtualize.

#30: Capitalism, ho!

Hint #1: You have to pay back the debt accumulated by your father by selling stuff, most of them being adventuring related. 

Hint #2: You get the items to sell at your store either from the quartermaster who supplies most of the (unseen) stores in town, from the little stalls at the market, but mostly from the dungeon since those are of course free. For this end you hire a hero to fight for you while you transport the goods you find in chests or from monster drops, hidden under a shield and invisibility spell, so only your chosen warrior can get hit.

#27: Game over, yeaaaaaaaaaaaah!

#26: This game is from a series of turn-based strategy games where you lead entire armies into battle, stack by stack.

#29: PC Building Simulator?

Yeah, that's too far I'd say.

Here are some more clues:

30.  There is a PS4 first party exclusive that is strongly inspired by this third party entry, the first time this franchise went open world.

Dark Souls?