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No, you don't need to end the orc war event, you need to go back to Victoria's dungeon and save Ste (I recommend using Arion to help save Ste). From there, you progress stuff with Ste to start the New Road quest (for the best outcome, make sure no one dies). Then you'll unlock the Country Road quest, and finish it but be careful you can lose a heart from both Ste and Logan. After that Logan owes you a beer in Bareshade, be careful here too if you sleep with him you'll lose a heart. If you've avoided all that you will get Logan's second heart

Nope, but you can start a new game, that's what I did when I missed one of his hearts 

Unfortunately, you have to go back to a previous save file where you can do the other Love Point options. The X means it's no longer available. Try going on the Lustful Desires Wiki, on there, you'll be able to find a guide on how to get all 3 of Logan's hearts and avoid losing them.

Does anyone know how to transfer save data from an older version of LD to a newer one on a MacOS?