An easy way to get more money is to pick your party then become a banker. Then go to your contract and hit accept once you are a banker.
You should be at the store. Buy the things nessesary. once you are out of cash but have supplies go out of the store.
Do Not Hit The Wheel! It will ruin everything. once you are out of the store go back to the hotel and hit your contract and change your proffession to something besides what you had in the first place. Then hit your contract and hit accept, you should be at a window that says hit the trail or go into town. Hit go into town and go to the store and click somthing (like the pig) and it should take you to the menu to buy somthing.