It depend on what you expect from Logan.
[SPOILER ALERT]
For Encourage option, it will lead you to 'Corrupted Logan' route aka. Bottom Logan, B! Logan. Which you cannot gain his like more than 30 and cannot gain any heart from him. But you can see him get fucked from various NPC in various events like Barrel, Korg etc. some scene has CGs too.
For Discourage option, it will lead you to 'Normal Logan' route aka. Top Logan, T! Logan. Which you can get more romantic relationship with him and also his hearts.
The difference of route make a difference for some scenes too. By the way, I have play all routes of him.