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Time for a correction. Turns out there is a way to guarantee a commission ticket every time the supply ship shows up. I discovered that up to HR20, a player will not get any weapons with the MISC choice, but will instead get 1 Commission Ticket, every time. Once you go and do the quests that allow you past HR20, then the weapons start showing up, thus dramatically reducing one's chances of getting the ticket. Hope this helps people who are still at a good stage before trying to jump too fast.
That's the point, the game itself handles autosaving, which allows for rolling, just like with crowns.
This isn't true, I successfully rolled tickets just yesterday, and there haven't been any updates since then.
The game now autosaves when you rest in your tent, so it's impossible to reroll Santiago's inventory. All you can do is rest for 6 days to completely restock his inventory with another round trip.