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When you reach a high level buy a club on Main Street or another place and decorate and add to that club so it's as good as your first club and you will get double the money. Keep doing this with all of the other towns and you will make millions in the process.
When you do challenges sell anything that is worth 100k+ and spend ALL the money on building your bar stock. You won't be wasting money because when you go offline you are still selling drinks so when you come back online you'll be richer.