Logan is very popular and I'm pretty sure he wouldn't mind even if he's a tsundere lumberjack lol.
There is so much possibility with the Satyr. He's one of the few enemies that doesn't mind defeat by sexy times (the surprisingly horny Northcrest guards are the others) so there's plenty of scenarios that can be think of that leads to a happy ending for all involved.
Ya both Troublemaker and Drunkard are watchmen I'm thinking we catch them during shift change at certain hours like in "Oh look fancy meeting both of my favourite watchmen at the same time. What a happy coincidence that I totally didn't plan for.." since our MC can be a sneaky bastard sometimes.
Both? There's many of em we don't have to put them all in one place. Maybe one we meet in the tavern when hanging out and they get flirty. Maybe another got defeated by us (or defeat us) at a drinking game and we have to bring them home or upstairs.. or ya we could just plain rent ourselves out or have fun in public. They could all be random events so there's more variety every time you go to the tavern or public.
Aww shame. Guess it will just stay in my dirty dream where they switch repeatedly.