Sometimes people may work in many states and will be required to file tax returns for many states.Real Estate Real estate is a common way to create a presence within a state that will mean filing a state tax return.Lottery or Gambling winnings There are any number of people surprised to find that they owe not only the feds but a state for winning a state lottery, winning the pot at a casino in another state, traveling to a game show and winning a prize.Business Income This gets much more tricky.

Now that also goes with your expectations of the economy, if you think in 5 years for example rates will drop, you could gamble, but conservative thinking says take the fixed rate.Rich, in your situation with all the property you have I doubt you're talking about a 30 year fixed with Fannie-mae.

If you are hiring workers off the street, that is a big gamble, as you don't know their history with law suits etc.

I sold one for $40K and 0ne for $45KIt is kind of like winning big the first time you gamble, now I am addicted to tax liens.Ned Carey

The gamble may payoff well.

Anything else is sort of a gamble.

Take a gamble on the inside.

I guess everything is a gamble with REOs and you never really know.

A lot of those areas are just starting to get new development so you are taking a gamble but if the area does turn you will bank.Who knew that Roscoe Village, with an average sale price of $800k, was an area you could not walk alone in at night 15 years ago?  

Now we are seeing excellent appreciation, but not uncontrolled to the point it is unsustainable.