XD Just like Red-King, I grew up with the old, old original Oregon Trail. But fortunately I've seen this version once or twice too. You rock for the shout out to the original, Redking!
If you're still taking names, I'll throw Ezekiel into the ring because I like the old-timey Biblical sound of it which I think fits very well with the overall theme of the game.
Sensei, how did you want to go about this Let's Play? I'd suggest
Teacher as a job because I think the increased difficulty would make it more enjoyable. However I want you to have fun playing it too! Teacher would be great if you feel up for it, otherwise Conrad mentioned Blacksmith which is a nice middle path (I've found Doctor to be even easier than Banker because of the bonus effect).
As for the start date I think
April is the best option. Of course if you wanted to make this impossibly hard you could always start in August.
With $400 dollars to spend, here's what I'd recommend:
8 Oxen-$160: If I recall correctly the amount of oxen you have controls how fast the wagon moves. More oxen in the beginning will help out the most in the long run, especially if any of them wander off or get sick or die. Oxen are also worth the most points besides people at end game.
10 Pairs of Clothes-$100: - Clothes can catch fire or get wet and anyone going naked is almost guaranteed to get sick. Plus Clothes are good trade items for Injuns or whatever else we need later in the game. Clothes and Wagon Parts are both worth more at end game.
3 Wagon Parts-$30 - 1 of each type. If we needed more of them for any reason we'd hopefully be able to trade for them latter on. Again Wagon Parts are worth more score at end game.
30 Boxes Bullets-$60 - With low cash bullets are going to be our main source of food. You can only carry back 250 lbs. from hunting, so try to only shoot big animals and 1 Caribou or Buffalo will give you more than you can carry.
150 lbs. Food-$30 - This really relies on you hunting for food no matter what so bad hunting can kill us. But we can't really afford to blow a lot of money on food with a Teacher's salary. You just have to be a good huntsman-surely learning to use a gun will help keep the schoolkids in line out in Oregon.
This leaves us with $20 spare cash. We'll need at least $5 for a ferry (I remember one river where you better damn well take the ferry) and maybe for more. It can also come in handy for trading if we need anything latter. However I don't think it will pay the toll at the end of the game, so we're definitely rafting down the river.
For food it should always, always be set at
Filling. The only reason we should ever change it is to avoid starvation if for some reason hunting doesn't go well or something. However, we should use a
Strenuous Pace, not a Steady one. Going at a constant steady pace will make us hit winter no matter what, and Grueling is the Pace you want to avoid. Strenuous should be the default, and we should only slow down because of disease or such.
How does that sound to you, Sensei?
Edit: Sensei if you do go with this it really, really depends a lot on Hunting. Also the first week of April or so can still be cold, so spending the first week or so hunting might not be a bad idea.