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In terms of skills, you unlock different classes as you play, and they will have slightly better at certain skill. And ou will gain skill as you use them during the game. Check this link on how to unlock https://indiefaq.com/guides/the-oregon-trail-all-classes-how-to-unlock-them.html
It is normal to need 50 days to heal a broken leg. The best way is to get to a fort and have the physician heal you for 30 coins.
Almost everything is single use. I think the only exception is the knife, but it will break after 3 to 4 uses.
If you are having new and don't know the game very well, try to start the game with the charming trait. You can get better deals with haggle. And wagon grease really helps too.
You can sell fish for $1 or $2 each depending on whether you haggle or not.
In previous games, you could just hunt whenever you wanted. In this one, you can only hunt when you either arrive at a hunting zone on the map or a hunting event happens.
Likewise, you can't just rest whenever you want; you have to actually encounter a campsite to do that.
Kind of confused me at first; when I'm low on food, my first instinct is to go hunting, and when someone gets hurt or sick, my first instinct is to rest.
If you have a banker in the team it helps because of the extra starting money but still... you cannot start with ammo and food and clothes, you have to sacrifice one of those and hope you get a trade opportunity for it early. Once you have prospector unlocked if you're lucky you can trade away your nitro (and you should, you don't want to carry this without using wheel grease).
It's a fun challenge actually, I quite like it!
For an easier start, it's better to use the default wagon with one of the starting kits.
This just means that you don't know the value of their skills yet, it doesn't mean 0 skill or that they are not good at it.
You have to try an activity related to that skill to reveal its value for each character.
The bait crafting is a bit weird, you can only craft bait before you fish, and only with "food stuff" (looks like a bag of berries) or fish. It is rare to get your hands on "food stuff" (random road event with raspberries) and your team is gonna eat that type of food before any other type as far as I can tell, so it is even rarer to find a fishing spot with enough "food stuff" left to craft bait. Your team eats meat before fish, so if you hit two fishing nodes relativity close to each other you can manage to craft a lot of bait.
Considering all that, buying it in a fort shop is the most reliable way to get bait.
There is a quest that can trigger at a fishing node with a npc that gives you some bait, not sure on which trail I encountered it, "Oregon or bust" I think.