Creating Strong Cash Flow
Please remember that when you have alot of property you tend sometimes to become a target.
You need to build your mafia big so you can get your hands on as many 'Mafia Mike's' bars as you can during the early phases of the game. These are cheap and give more cash flow than buying any of the other smaller properties. The only thing you need for more bars is a bigger mafia, so keep the recruiting up on a daily basis. You'll need them to guarantee the upkeep of your vehicles and heavy weapons which are required for the bigger jobs. Recruit constantly to your mafia and keep buying bars to keep up with your numbers. You should quickly be able to have a cash flow of over $200,000. Bars are also great because they don't require protection from robbing. It's a good idea to make bars the base of your property dealings and only get into the bigger hotels and casinos once you're bringing in millions in cash flow AND have a strong enough mafia to repel heists.
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It's not a good idea to sit around on a lot of cash. Always put it to work for you. If you just sit on it, you can lose a lot of it in a fight and your hard work will go to other mafias. Always buy property in bulk when you can to get it at the lower price. You pay more 1 by 1. Doing big jobs will bring in lots of money very fast. Reinvest it quickly into property. That's good business. Instead of looking at the money, invest it into making you MORE money without having to work for it in jobs or fights. I don't recommend buying ANY rent houses or Italian restaurants. The cash flow is too little. Focus on bars until you can afford hotels and casinos. Remember the movie The Godfather? Did you ever see Al Pacino and the Corleone family worried about rent houses or restaurants? No way, because it's not good cash flow. Hotels and casinos is where the big money's at. They're expensive to protect, so don't lighten up just because you got the properties. Once you have a large mafia and lots of good defensive loot, go ahead and go for casinos and hotels, but until then make do with empty property and Mafia Mike's bars. There will be plenty of time for the big hotels/casinos later.