I think you have enough like for him. If you said you have camp's moral (not Bandit affection, it's not the same thing) more than 25 and Green ending in Northcrest conspiracy event, there should be Belly fun appear in talk option.
That's weird, have you tried to re-download the latest version again? If you already try and not work, please try to play with these save files of mine. Please read the instruction well to prevent your loss of game procession.
For "Check on what the thug is up to" option, you need to have a love potion in your inventory. And another requirement is the same, you need to play in the green route of Northcrest conspiracy. And for Belly fun, if you sure you have all requirements met, it should be show in talk option like here.
I'm 100% sure I have all the requirements met. Next time I go on, I'll grab three screenshots to show you just how weird it is.
I'm trying to just get the option with the wrestling with Barrel. He shows up and there's 2 options - fair fight and throw the fight. No matter what I pick, he never shows up at my house in bareshade.
