Thanks for the super detailed feedback!
Under-the-hood skillchecks mostly depend on your team's skill set (a few are straight-up luck). E.g. if something spooky happens, you might have a resilience check against the team member whose resilience is the lowest. Or if you're trying to operate the mining laser, that's an education check against your highest education crew member. If your crew are red for all stats, you're gonna have a bad time.
I went back and forth on how much to reveal what a decision would do, and settled on having subtle hints in the text rather than something like a difficulty icon (mostly because of limited time to be honest!). For a future version, I'd probably add a simple visual indicator that shows whether a decision is luck-based, an easy fitness check, a hard survival check etc. The intention is definitely to be more about resource and skill management (and crew management) than bad luck. Ultimately, it's about creating stories (some of which end up with your crew going crazy or being blown up).
You're also correct that I intentionally leaned towards more difficult and punishing outcomes given the theme and the limited time that people have to check out games during this phase. A more developed version of Extraction would probably have longer missions that gradually change in difficulty over time.