That doesn't seem like a good investment to me, it becomes very much a gamble on appreciation. 

Is it a gamble?

This has had some success with people who had been living in prime locations like Paris for 50 years.The gamble of course is that this 75 y/o still gets to his or her centennial.

You make a very interesting point that I didn't even think about how some agents take a gamble working with people for weeks or longer to only realize that they don't have funds to close.

If you're going to buy foreclosures at an auction there's going to be some aspect of gambling involved.

Other investors gambled, overpaid, negatively cash flowed, and got wiped out.

Real estate is a big lumbering elephant compared to the nimble stock market, but it's still a gamble to wait to time the market for downturns and upturns.   

Then again, maybe not...it's obviously a bit of a gamble. 

Sure, maybe the market doesn't tank, and you don't care about cash flow, because by god Boston is so great and its nothing but upwards from here, but my preference is not to take that gamble and find higher and more predictable returns in other more accessible markets.

As a result it is currently listed on AirBnB.Thing is I feel worried cuz we gambled on our first property, looks to have worked out good.