If you want to become rich fast just use my method
Character creation
Pick all the following options:
Pick Ironborn (So your army doesn't lose morale when sailing, though isn't necessary)
Father: Merchant
Childhood: Merchant's Apprentice
Vocation: Merchant
The Rest is up to you, how you spend your skill points doesn't really matter since you are already, 6-7 in trading, 4-5 in persuading and 3-4 in pathfinding.
In-game
Run straight to Winterfell (Remember to visit The Old Stone bridge to get free XP and to visit The Crossroads inn and get Sir Janis Lyren to join your army)
Once you arrive at Winterfell sell your goods that you start with, and buy furs (furs will get even cheaper as you progress) Once you have bought a small number of furs you go to Fairmarket and Riverrun to sell your furs, afterwards you buy salt and sell it to Winterfell. (Continue this route until you'll have money in no time)
You can develop this trading route by Buying furs at Castle Black, Winterfell and Barrowton, sell the furs at Fairmarket and Riverrun, buy salt and sell that at Lannisport and Kayce, once you've sold your salt buy Iron and stone from both Lannisport and Kayce (Iron and stone can literally be sold anywhere for a good price) Continue this route and you'll be the richest man known to mankind
EDIT: About the ship, sail to Essos and rebuild the ruined-Castle, this should supply you with enough stags to manage the up-keep for your troops (Assuming you don't have the largest army with you on your merchant routes)
Character creation
Pick all the following options:
Pick Ironborn (So your army doesn't lose morale when sailing, though isn't necessary)
Father: Merchant
Childhood: Merchant's Apprentice
Vocation: Merchant
The Rest is up to you, how you spend your skill points doesn't really matter since you are already, 6-7 in trading, 4-5 in persuading and 3-4 in pathfinding.
In-game
Run straight to Winterfell (Remember to visit The Old Stone bridge to get free XP and to visit The Crossroads inn and get Sir Janis Lyren to join your army)
Once you arrive at Winterfell sell your goods that you start with, and buy furs (furs will get even cheaper as you progress) Once you have bought a small number of furs you go to Fairmarket and Riverrun to sell your furs, afterwards you buy salt and sell it to Winterfell. (Continue this route until you'll have money in no time)
You can develop this trading route by Buying furs at Castle Black, Winterfell and Barrowton, sell the furs at Fairmarket and Riverrun, buy salt and sell that at Lannisport and Kayce, once you've sold your salt buy Iron and stone from both Lannisport and Kayce (Iron and stone can literally be sold anywhere for a good price) Continue this route and you'll be the richest man known to mankind
EDIT: About the ship, sail to Essos and rebuild the ruined-Castle, this should supply you with enough stags to manage the up-keep for your troops (Assuming you don't have the largest army with you on your merchant routes)