I just managed to play my first game of Wayward yesterday. I really enjoyed it. Two players went for the lockpicks, the third had no clear cut strategy, mostly due to bad luck and taking risks (the God of Gold was not kind to him).
The last turn race for the end could have honestly seen any, or none of us, make it out. Very fun.
The rules are pretty clear, no issues really. I just wanted to clarify "random item rolls". If you are acquiring or losing items, and the roll is not reflected on the sheet (for example the lockpick section, 4+) that means you don't get anything (or lose anything), right? So you could get cursed but not actually receive a chip? Or the squid doesn't actually take anything?
For random items (receiving an item, receiving a cursed item one or losing an item), if you rolled the lock pick section, then rolled a 4+, you would not receive a lock pick, receive a cursed lock pick or lose a lock pick.
Hope that helps,