So what I'm doing on my current playthrough of the game now is that I don't plan paying anything except for work that is done to my cars at any of the body shop's in Empire Bay.
If I need new clothes to wear I steal it from a store and take all their mony too.
wow..now u're thinking like an old school mobster . i did exactly that on my third play-through. mostly i just like to drive around feeling how things must have been during WW2..the sights..sounds...everything.