I have a one year rule where I wont re-play a game for at least year minimum.
Also if the game is multiplat, I would play it on another platform if possible.
Prime examples would be like
Devil May Cry (PS2): 81
Devil May Cry HD (PS3): 81
Devil May Cry HD (PS4): 82
Devil May Cry (NS): 80
Devil May Cry 2 (PS2): 60
Devil May Cry 2 HD (PS3): 60
Devil May Cry 2 HD (PS4): 60
Devil May Cry 3 Dante's Awakening (PS2): 95
Devil May Cry 3 Dante's Awakening Special Edition HD (PS3): 98
Devil May Cry 3 Dante's Awakening Special Edition (PS4): 99
Devil May Cry 4 (PS3): 87
Devil May Cry 4 Special Edition (PS4): 89
DmC Devil May Cry (PC): 88
Final Fantasy I Dawn of Souls (GBA): 82
Final Fantasy I Anniversary (PSP): 85
Final Fantasy I (iOS): 81
Final Fantasy I Pixel Remaster (NS): 87
Final Fantasy II Dawn of Souls (GBA): 83
Final Fantasy II Anniversary (PSP): 85
Final Fantasy II Pixel Remaster (NS): 87
Final Fantasy III (NES): 80
Final Fantasy III Pixel Remaster (NS): 90
Final Fantasy III (DS): 86
Final Fantasy IV (SNES): 90
Final Fantasy IV (PS1): 89
Final Fantasy IV (GBA): 86
Final Fantasy IV (DS): 92
Final Fantasy IV (PSP): 94
Final Fantasy IV Pixel Remaster (NS): 95
Final Fantasy IV After Years/Prologue (PSP): 88
Final Fantasy V (SNES): 84
Final Fantasy V (PS1): 83
Final Fantasy V Advance (GBA): 88
Final Fantasy V (PC): 91
Final Fantasy V Pixel Remaster (NS): 93
Final Fantasy VI (SNES): 95
Final Fantasy VI (PS1): 94
Final Fantasy VI Advance (GBA): 95
Final Fantasy VI (PC): 97
Final Fantasy VI Pixel Remaster (NS): 96
Final Fantasy VII (PS1): 93
Final Fantasy VII (PC): 93
Final Fantasy VII (NS): 94
Final Fantasy VII Crisis Core (PSP): 93
Final Fantasy VII Remake Intergrade (PC): 100
Final Fantasy VIII (PS1): 88
Final Fantasy VIII (PC): 88
Final Fantasy IX (PS1): 95
Final Fantasy IX (PC): 97
God of War (PS2): 85
God of War (PS3): 86
God of War II (PS2): 90
God of War II (PS3): 90
God of War III (PS3): 95
God of War Ascension (PS3): 80
God of War Chains of Olympus (PSP): 80
God of War Chains of Olympus HD (PS3): 81
God of War Ghost of Sparta (PSP): 85
God of War Ghost of Sparta HD (PS3): 86
Kingdom Hearts I (PS2): 96
Kingdom Hearts I Final Mix (PS3): 97
Kingdom Hearts I Final Mix (PS4): 98
Kingdom Hearts II (PS2): 96
Kingdom Hearts II Final Mix (PS3): 97
Kingdom Hearts II Final Mix (PS4): 100
Kingdom Hearts Chain of Memories (GBA): 81
Kingdom Hearts Re:Chain of Memories (PS2): 88
Kingdom Hearts Re:Chain of Memories (PS3): 88
Kingdom Hearts Re:Chain of Memories (PS4): 90
Kingdom Hearts 358/2 Days (DS): 86
Kingdom Hearts Birth By Sleep (PSP): 97
Kingdom Hearts Birth By Sleep Final Mix (PS3): 98
Kingdom Hearts Birth By Sleep Final Mix (PS4): 99
Kingdom Hearts Re:Coded (DS): 73
Kingdom Hearts 3D Dream Drop Distance (3DS): 90
Sonic the Hedgehog (SGEN): 77
Sonic the Hedgehog (PC): 80
Sonic the Hedgehog 2 (SGEN): 81
Sonic the Hedgehog 2 (PC): 82
Sonic the Hedgehog 3 (SGEN): 78
Sonic & Knuckles (SGEN): 78
Sonic 3 & Knuckles (PC): 86
Sonic the Hedgehog 4 Episode 1 (PC): 83
Sonic the Hedgehog 4 Episode 2 (PC): 90
Sonic 3D Blast (SGEN): 56
Sonic 3D Blast (PC): 57
Sonic Spinball (SGEN): 49
Sonic Spinball (PC): 50
Sonic CD (PC): 83
Sonic Adventure DX (PC): 84
Sonic Adventure 2 Battle (GCN): 94
Sonic Adventure 2 Battle (PC): 93
Sonic Unleashed (X360): 70
Sonic Generations (PC): 96
Sonic Generations (3DS): 53
Sonic Lost World (PC): 81
Sonic Lost World (3DS): 52
Sonic Mania (PC): 94
Sonic Forces (PC): 87
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If a game has New Game+ that leads to multiple endings like Chrono Trigger's system, I would play it immediately otherwise I barely play New Game+