A few tips (Add more in comments)

[Daughterof Maat]

1. When you get the Tranquil Trail use it all the time. It's much easier and you get more money
2. If you fail a river crossing and can't go on, exit out of the game and then go back in. You will be placed before the river once more.
3. If you want to fish put a minister or doctor on your team. Their attitude should be higher and high attitude is fishing success. Musicians too.
4. Always keep some bullets handy from the Blue Mountains onward. You may have to shoot an attacking bear.
5. Don't worry about spending money in the beginning. It's worth it. Many money opportunities will come to you.

[nintendogamer192 ♥♥♥♥♥♥♥♥.com]

What is "Tranquil Trail"

[HMS_Indefatigable]

My biggest tip is that axle grease is fantastic - buy every bit of it you can, trade for it whenever possible, aim to have it active for almost the entire trip. You end up saving loads of room vs having to carry a lot of spares or tool kits, avoid having to drop things overboard due to damage/losing them to uncovered tiles, overall save money vs buying spares and tool kits constantly, and save energy and time otherwise spent trying to fix the wagon during carpentry skill checks.

[Goof]

Originally posted by HMS_Indefatigable:

My biggest tip is that axle grease is fantastic - buy every bit of it you can, trade for it whenever possible, aim to have it active for almost the entire trip. You end up saving loads of room vs having to carry a lot of spares or tool kits, avoid having to drop things overboard due to damage/losing them to uncovered tiles, overall save money vs buying spares and tool kits constantly, and save energy and time otherwise spent trying to fix the wagon during carpentry skill checks.

yes. grease is op