My idea for the first tiny bit of the trailer would be:
Start with "You have died of dysentery... and robots" as a great opening line for the trailer (and then we leave it at that as far as Oregon Trail references). Then people are looking at it through the OT lens immediately, and we can commence with the unique things.
The second block of text could be something along the lines of "Plan For The Long Haul: Every expenditure of ammunition, fuel, food, or health is permanent in your campaign."
With accompanying visuals and pacing and all that to support both things, and then moving into other things that are unique and interesting. And for that second line, that may or may not get pushed further back in the trailer depending on if we come up with something that is even better than it. But I think that's a pretty cool second hook, and the first hook that makes people think of OT is something that is clearly already working wonders to make people excited.
It's going to be hard, because opinions are going to very wildly.
For me, you would first setup the setting, and then the "hook" and from there explain and give shout outs.
If you give a shout out first, you polarize to those who get the reference. If you give the setting and hook afterward, you are then trying to appeal to those who like the shoutout. If you give a shout out first, that shoutout will be on the viewers mind the rest of the trailer, and will be viewed with the OT lens for better or worst.
If you give the setting and hook first, then the setting and hook get the full attention of the viewer. Nothing wrong then from fleshing out and giving various shout outs.
In my opinion, the second approach will give better results then the first: You will get more sales by telling the hook before bringing up previous games rather then bringing up previous games first. It helps distinguish your game. To put another way: The first point you bring will be remembered most, so make that your game, not another one.
<Just to clarify my biases, I love FTL aside from the forced saves [which can be circumvented.] I do NOT like Oregan trail.>