I think it should be a comedic style trailer. An example, start off saying it's the most interesting thing in the world much like many other trailers, and then shift to the game where all that would be heard is the music and the texts. Make it something that would make anyone smile. That's what I would do anything. ( in a world of endless possibilities, only you can decide if they live or die...the choice is yours) make it way funnier though than I can.
Could try making the trailer cheesy, like the guy on the trail is talking to you asking you for help.everyone loves a Cheesy trailer. Show the game, the menu and all the choices you have to make but do it in a Cheesy funny way, and then after that introduce yourself and what you're trying to do with the game. And remind people of how fun the original Oregon Trail was.
What about a montage of the failure statements (ex: You have died of dysentery), in the old IBM type font on a white background, with an audio effect like the orchestra hit or whatever sound effect they use when bold print appears on screen. Have the speed in which the statements appear increase until they are too fast to read. Then stop....white screen for a moment...then another statement "No one said ______ was easy", with ___ being survival, or pioneering or a single word you would use to describe the underlying theme of the game. Then cut to a several images of the game with those end game scenes, add quotes like "Game Magazine says 5 stars" and "Your choices impact your results" and things like that. Just saying... :)
I'd basically approach making a trailer for this the same way I would for a visual novel, because of the text basis. You can take some of the premise-establishing text from the game and display it as part of the trailer in a dynamic way rather than just as text in the game itself. A trailer doesn't have to include just footage straight from the game.
Don’t try to make it seem like something it isn’t, but definitely go overboard with the screen effects? Example; *Main Title Screen, font comes spinning out of explosion 80s style to read “Cartier Trail, coming soon” sick af
Personal opinion - if you're super stuck and want to make it easier for yourself, pick some key phrases that define the game and then display content that illustrates them. For example, to show "your choices matter" you could feature a short clip of the repurcussions for one of the events. This is a bit of a cliche trailer but it does the job, especially when you're an indie developer without much time or resource on your hands
Honestly, I think the ideas you've gotten are great. It's also important to remember that this is almost catering to a slightly nostalgic audience, so seeing something that reminds them of Oregon Trail will already spark their interest.
It may be important to note that I didn't play Oregon Trail before seeing this project (though I've played it now). I liked the idea of choices and consequences, so maybe show that too?
At the end of the gameplay footage, don't forget to introduce yourself, tell more about what the player can expect form the game and, most importantly, explain why did you want to create the game in the first place. Be honest with your answers.
you could start off by showing the main menu of the game with a few seconds of the soundtrack then start the game. You should market the thousands of possibilities and show a lot of different deaths. Of course, telling the plot of the game is good too. A fun montage of the possibilities with that nice soundtrack should be fine.
You ever seen the trailer for Organ Trail: Director's Cut? Thats a decent way of making a boring game look more exciting lol.
you want to fade into a really important conversation, show the player (you + cursor) decide something, and then have something dramatic follow (i.e. you decide to hide the package behind a tree.... fast forward to the carrier's beheading beacuse he lost the package) or something.