So, how to progress Gin (I'm not sure yet)
First, you need to train him as much as possible until you'll see 3-4 points for training (feet's, ass, tits and hands if unlocked)
Then you need to walk around whole map and sleep on every bed you see. When you'll see Gin AND Cassie, just see the scene (I didn't told Cassie where's Gin).
Then walk around until Gin disappear again. Approach him and try to come closer. Done. When he'll run away to his usual place enjoy the result:
from what i found you can reload the area by leaving and entering the abandoned town, it takes quite a few tries to even get gin to go to the lake, and even more to get cassie to to go there as well. you can just cycle it. but doing so doesnt progress anything....although once there they dont leave, but cassie also goes looking for apples, so you need to keep going there incase shes there so you can re-roll for her to be at the lake...
I was walking around WHOLE map: New Ark, Desert base, milk farm... Just walking with hope to trigger character Cassie to go outside and Gin to go to lake. I said about sleeping with hope that it matter AT LEAST something as well.
I have no idea how EXACTLY scripts working, but I HOPE I'm triggering event's correctly
I have a much more efficient method. First, train Gin. If you're already in the 2 roleplay options and you're aiming for the third scene, make him wear a maid costume. Afterwards, leave the town and sleep.
If you get back and he's gone, don't go into the lake yet. Check the safehouse first if Cassie is there. If she's there, leave the town and enter again. Gin will still be in the lake so you just need to check the safehouse every time you enter. If Cassie is finally gone, you can check the lake and there's a huge chance they're both there.
You can also check the apple trees for Cassie first to make sure but I find that a bother and just prefer to save before checking the lake and reloading if she's not there.
