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

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! 

This is a gamble though, because you are not sure how long she will be alive for, and you cannot foresee future market conditions.

I would not want to gamble my personal money on pricing services that have just called around to formulate unit prices.Lastly, I know everyone want to be on a budget and save money where possible.  

If you gamble - diversify.

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.

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.

At some point we will encounter a correction but I would not gamble on it being imminent.  

Is this kind of just a fly by night gamble type of deal?