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.  

The one of them  wanted  to go for offshore fishing , and decided to rent a boat and then after some photographs  I showed them , resulted in renting a Yacht  65 feet .

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

The only way this becomes good is appreciation, and to me that's a gamble.

We usually sell our foreclosure properties for a profit but thinking you could turn $500 into $80,000 on one deal is not investing it's gambling.

I'm no good with a hammer, not interested in flipping which seems too much like gambling at this point in my life.

If we ran it for a year and worst-case a renter who's unhappy with us attempting to raise/normalize rents reports the leaking roof, we could be stuck with MAJOR repairs that we can't yet afford, or who knows, a condemned building because there's mold in that roof/attic/walls that have been leaking.It's discouraging - we could walk away and take our $25k and go 20% down on a duplex that cash flows $300 a month, or we gamble on this place where the cash flow is approaching $1.5k per month after budgeting conservatively with the bigger pockets calculators.