I used to gamble and was pretty good at it, especially blackjack  / 21. 

He is planning to move across the border to MN (much cheaper health insurance) and live in a house and step away from day to day activity. 

@Chandra Sekhar What border of South Shore? 

A lot of investors (and residents) try to stay in Columbia County which is the border county to the north.

It borders on mortgage fraud.

It's the area that sort of borders East Liberty and Lincoln-Larrimer.  

In every project someone is taking a gamble.

Of course, you can never wait until you have everything, but it seems like there is significantly less one has to work with before starting real estate investing, making one's attempt feel more like a gamble than a calculated risk....Or is there?

I have grown to like the NW Indiana market vs IL due to manufacturing/industrial companies moving across the border, landlord friendliness of IN, cheaper taxes and it will also give me the opportunity to get started sooner with the price of homes.

As another post mentions above, the antiquated municipality system generates wildly varying tax rates in communities that border one another.