The Oregon Trail 5th Edition (Teacher- Trail Guide)
Starting in March 1840, going from Independence to Willamette Valley (Oregon City), I kill the default high scores and have all 5 members of my wagon survive. The entire animated series is shown along the way as well.
On an aside, I think Adventurer is the hardest difficulty, although it’s played to be the “Medium.”
Trail Guide gives you an extra $500 shortly after you set off, which greatly reduces the amount of hunting/fishing needed to complete the game with one of the lower starting cash occupations. It’s balanced by having the game end if wagon train morale dips too low, which you either have to be extremely stupid, or try extra hard to fail in order to have it happen. I’m talking buy 5 grandfather clocks at the beginning, rub salt in gunshot wounds, and pack frostbitten limbs in snow while backtracking the Hastings Cutoff in December kind of effort. A full party kill is easier to attain than getting removed as leader.
The only differences between Trail Guide and Adventurer are that as an Adventurer you can continue the game if you’re demoted from train leader (computer picks which way you go though there’s a chance you can get re-elected to commander, sometimes in a day our two after demotion), and you don’t get the extra $500 when you’re promoted. The lack of money means more time spent hunting, fishing, and gathering to ensure survival with the lower starting pay occupations. That makes “Medium” more difficult than “Hard” I’d say.