Randomly Lost Progress In My Game

olyviarose13 Thanks! These are modded saves.  I'm ignoring those as there is a Mods forum for Mod specific issues you would need to post in here if you want them to load - The Sims 4 Mods & Custom Content | EA Forums :

/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000007.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000006.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000004.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_0000000B.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_0000000C.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000005.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000000.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_0000000D.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000002.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000003.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_0000000E.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00001112.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00001113.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00001111.cwd
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/WickedWhimsMod/complex_save_data/ComplexSaveData_Slot_00000008.cwd

These are saves in the correct location and should load:

/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000c.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001113.save

These are backups of those saves and will not load unless you remove the .verX from the file name:

/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001113.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001113.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000b.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save.ver2
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001113.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save.ver4
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001113.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001111.save.ver3
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000004.save.ver1
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00001112.save.ver0
/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_0000000e.save.ver0

This is a duplicate backup save. You can tell because the OS has added "2" to the file name after .save because you cannot have two files with the same filename in the same location:

/Users/olyviarose/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save 2.ver0

These are all in OneDrive and will not load because a) they are not in the correct location for the game to load them and b) because again the OS has added numbers before .save. They look like some sort of backup of one Slot_00000002.save but you have multiple copies:

/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 7.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 6.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 3.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 2.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 9.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 5.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save 2.ver0
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 4.save
/Users/olyviarose/Library/CloudStorage/OneDrive-Personal/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 8.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 7.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 6.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 3.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 2.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 9.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 5.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002.save 2.ver0
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 4.save
/Users/olyviarose/Library/Group Containers/UBF8T346G9.OneDriveSyncClientSuite/OneDrive.noindex/OneDrive/Documents/Electronic Arts/The Sims 4/saves/Slot_00000002 8.save

Your game will only load saves if they are directly in User > Documents > Electronic Arts > The Sims 4 > saves and only in the format Slot_XXXXXXXX.save (where X can be a letter or number). Anything outside of this and it is ignored. You'll have to figure out the modded saves files issue yourself.