But it's a gamble, right?

It's a gamble if you just leave them in random places.

One CASH flow is everything and the only reason to own rentals is to get the max amount of cash flow possible and appreciation is gambling luck or whatever. 

Another thing, even if you find a partner who can put in the capital, do you think he/she will be willing to gamble their money with a newbie?

So here they are spending thousands of dollars, with full confidence when they are literally gambling with their money with the odds being against them.See it this way.

I purchased a primary residence that will become a rental in 3-5 years.It doesn't cash flow as is (if I rented it today), but the area has high appreciation.I wanted to start with a great numbers to start, but being military and needing to find my family a good home, I took a gamble.

I imagine people or doing it anyways and just gambling on not getting caught.. what are your thoughts?

Other possible projects on the horizon like increasing the size of the offshore wind farm have been proposed, which would also add high paying jobs and demand for properties.Value is is already gone in most of the nicer parts of New England.

While I don't have any investment real estate yet, I can say that if you are a gambling person you can work without the safety net of a LLC or S corp.I have started llc's for both investment and management upon the advice of attorneys in Wisconsin.

For bank financing you're out of luck because you have to be a resident to have off-shore income taken into account for your credit-worthiness.