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.   

So no negotiations need just needed to figure out what to do with it that ignited my passion in investing.

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.

Outside of that, I convinced her it's taking a gamble on me overall, but that my track record professionally and personally justifies it.

I think it's a good place to get a bit of cash flow and appreciation without making a huge gamble like a lot of the folks 30 miles north are doing!