I think that this will probably change later. This thing about Bareshade Expansion needing you to have X hearts with him. Hyao still is writting the and can always change something. Your point is valid and understandable.
About the New Road event, I don't know exactly gow to help you since I've done it just once. What I suggest you is:
1 - Try gaining more hearts with Bernard.
2 - Bring Caleb back and finish the Full Moon storyline
3 - Start and finish the Bareshade Expansion
After those things done you'll be able to have a special day in Bareshade weekly, it's a fair.
With it being unlocked you'll be able to invite different NPCs not-Bareshade-citizes to party in. I THINK it will trigger you a new topic with Ste and I THINK he'll say something about it being better with a sortcut. Then, try talking with Logan about it.
I know it's not good to have this kind of interaction with them, but in the last case you can just skip the dialogues and get the heart.
I thought that a way to solve this thing of needing to have X hearts with X NPCs to progress in-game even though your character are not romantically atracted to them could change the hearts meaning to not just a platonic stuff but some kind of trust level.
The scenes you'd get trying to get hearts with them when you MC is not into developing a relationship with the gender of the NPCs would be changed by some more deeply-bond friendship which they start to trust you and see you as a great friend.