Here is the full list of all 19 Obscure achievements. It takes around 12-15 hours to unlock all of the achievements on Windows.
Every playable character survived at Leafmore.
Finish the game in 'Special' mode.
Finish the game in 'Hard' mode.
Kill 150 monsters with a firearm.
Finish the game.
Finish the game in 'Normal' mode.
Kill 3 monsters with a single light grenade.
Cross the gardens.
Enter the gardens.
Check out the dorms.
Search the basement.
Search the auditorium.
Go to the nurse's office.
Explore the library.
Find the principal.
Leave the office building.
Finish the prologue.
Find all of the weapons.
Kill 50 monsters hand-to-hand.