Be cautious moving forward on filing insurance claims or all of your cash flow with be eaten up by insurance costs lol. 

DTH  I would be cautious going into business with friends or family.

One option for you might be turnkey properties in cash flowing markets, just be cautious and make sure you choose a reputable operator and run your own #'s (don't just use theirs). 

I am that kind of guy that enjoys a little fun, and let my cautious neighbors understand that I shoot back and dont call 911!

So tread cautiously 

I have been extremely cautious about telling my co-workers about my investing.

I am cautiously for this plan , but know we have a long way to go to make health care work in our society.

Am I being overly cautious? 

If it is west of Highway 51 we will be more cautious and if it is in the northern part near the Links at Davy Crocket golf course we will also stay away from it. 

And it is important to keep in mind that cash flow is just one driver of your returns: you also are paying down the principal and reaping potential appreciation, though the latter is not guaranteed.Investing in a property with negative cash flow can definitely work, and I view it as a sign to slow down and move cautiously: make sure the neighborhood is good, make sure the house is in good condition or that the current condition is reflected in the price, etc.