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Starting My stratagy works for version 1.2 of Oregon Trail. When you start at Independance try to buy as much supplies as you can. I usualy start with 8 Oxen, 1 set of clothes, 1 of each wagon part,20 boxes of bullets, 1 lb of food. Once you begin hunt immediatly until you have over 200 lbs of food.
Making Money most people don't know that it's possible to make money on the trail. To make money start by pressing trade and try to get 5 oxen. Only accept offers under 100 dollars. Once you do that trade to get 100 dollars, and only accept offers of four oxen only. After this you will have an extra oxen and some additional profit. You can also trade for higher prices that the fort sells and whenever someone accepts you can then go and buy it from the fort for a profit. Repeat until you are satisfied with your cash. If you do this process doing it at a river won't allow time to pass.
Making List of Legends I always start as a teacher so that way my final score is multiplied by 3.5. Also the more food and supplies you have the more points you receive so hunt a lot before ariving at Oregon. Prevent deaths by always resting when someone gets sick or is betten by a snake, rest until they get better.
Other Info. When you cross the snake river you have the chance to hire an Indian Guide for 1-5 sets of clothes. The less buffalo you kill the better deal you shall receive. The max amound of perishable food you can have is 985 lb. the maximum amound of weight that can be carried back after a hunt is 250 lbs of food. The average buffalo weighs more than 250 so don't shoot more than 1. Always keep your food as high as you can and your pace steady. This improves health and lowers the chance of wagon wheels breaking.
Land Marks/forts When you rest at a land mark people often heal quicker than on the trail. Also resting longer at places like Soda Springs allows you to get fresh water and lower your chance of getting Dysentary. Prices get higher as the farther you go. Oxen go up to 5 dollars at each fort. Clothes and wagon parts increase 2.5 dollars. Food increases .10 dollars and bullets increase 2.5 dollars. Always try to trade for your materials before going into forts to buy them. Usualy trades get you a better bargain.
Crossing Rivers Usually it is safe to caulk the wagon and float it however if the river is to high don't do it, instead take a ferry. Although it's rare ferries can run up against the bottom of the river if it's too low. If the river is 1.0 ft or below ford however never ford if it's higher. At the end when you reach the Dalls don't raft unless you are happy with your amount of food, cash, health and supplies. If you aren't, then rest up before taking the toll road.