It only looks like it, I generally try to keep as simple as possible. I'm not clever enough to make some thousands-variables complex system.
Have you considered making the reporting of this event a separate automatic event the next day on Despina instead of baked in into Tess day 2?
Its not a huge problem, but if you dont mind the feedback i dont think its ideal the current way. The player could miss it entirely despite wanting to tell them. My reaction was, holy shit, i need to run to bay9 and round up the officers asap. I imagine they would thank me, toss me out for the day and start brainstorming if they need to recall the whole crew early, if they can/should finish loading cargo, if they should fight maybe. (ofc the player doesnt know enough about them yet for me to tell if they'd consider fighting). Time might be of the essence if pirates will recruit forcibly for this or take ships to use them. Having the telling be part of spaceport day2 would make even more sense to me. So even waiting and doing Tess day1 as if nothing happened (which would also be the route for some ppl) doesnt quite sit right.
The other option you might want to consider is limiting (some) choices of places to a certain order, in this case making Tess day2 available after spaceport day2. Sorry for the unsoliticed advice i know nothing of your gameplan. But if any event can happen in any order that cant be good once the events start affecting eachother.
Who the player will want to share the info with depends on who we like the most. But the Despina crew is one big group of maincast the MC plans his future with so they automatically make sense as a choice.
The "I shouldnt tell you this ,but.." line suprised me a bit, wonder what was MC thinking about saying that? It sounds like not fully trusting them, but to me it felt like we should be past that, they could be MC's escape route. Whats more, breaking the news is a way to earn their trust and appreciation once some of the news is confirmed. I am glad Tess takes it seriously btw.
Minor issue and i wrote a whole page about it, im just invested in the story X).