Yup, Hitoba is right. Certainly the gang are lucky. But properly using luck or dealing with unluck is a skill too, and business are often down to luck too. There are plenty of stories about product that somehow just manages to be popular somehow, and product that fail despite a lot of effort spend. Or stories of some idea person got rejected by many companies until they found one who are willing to try their stuff and make bank afterward.
This arc is actually a good example of that, sure they are lucky meeting Hitoba with her sweet-making talent, but also unlucky in how she is a compulsive gambler. Most people would have cut her away, but Chie keep trusting her and help her to become productive.
The gang is reckless. .. but the other hand, it is alright-ish to be reckless to a point if you can still afford it. For all that their big spending, they are still solvent. Even if they spend all their money, as long they stop before going into debt, they'll just back to normal life.
