No, you are not supposed to go back to the island in chapter 2. You can go back to the island repeatedly in Chapter 1 to get all the storylines there. So if you're stuck in chapter two, it is helpful to post a screenshot with all the quests you have done.Are we supposed to go back to the island during chapter 2? I don't have any more events on the yacht(stuck at "Progression Tracker" - 39% & "Island": 57%) and if I do go to the island by talking to Rachel, the folder I downloaded from the op doesn't contain any images of the island. I tried downloading the game from the patreon page as well, but the island images are missing in there too. The game works, but only shows the ui.
I do remember from my playthrough that at some point I had just one quest active, while another 30 or so where waiting for some event triggers. So it is possible that you are experiencing something similar.