I just think it might be really easy to be exploited as a beginner.  

I went into it knowing there was sweat equity and i was ready to exploit it.The thing about Real Estate is most people aren't hitting home runs by waiting for the perfect pitch and then swinging for the fences...they are hitting home runs by taking what the pitcher gives them and then consistently hitting singles/doubles and then occasionally they hit one out of the park (as is this example)***Anyways,We noticed this was a very large 2 bedroom home in a nice location.

I attended a landlord bootcamp which I HIGHLY, 100% RECOMMEND even well experienced landlords go to, not the city run one, which I also have been to and came away thinking it should be called the "tiny bit of good info and LOTS of veiled threats if you're a future slumlord class" but its from the Apartment Assoc of SE WI (I'm a member for full disclosure) but you'll get 8 or 9 hours of PRICELESS info directly from the attorney who my usual, general practice lawyer said is hands down the one to call for any bad eviction or potentially big liability type deals and he'll go through things that the city for one, would never dream of telling you, such as how in Milwaukee Cty, our judiciary is very biased to the left side of politics as you'd guess for a generally left leaning county, but that many of these judges take those political stances right into their courtrooms and you sure as hell better be prepared for rulings that fly in the face of the current laws, especially the changes made a few years back when the GOP gained TOTAL control of state gov't in legislature as well as the governor seat and as was national news at the time, went like a machete through the law books and fixed a lot of things needing fixing, including several relatively minor aspects of landlord/tenant laws that COULD be exploited, as well as stuff that didn't make sense anymore, etc.

Maybe there are legal loopholes that one can exploit,without ending up in the pokey.

Personally it sounds like this tenant exploited your kindness and took advantage of it.

Greetings, I'm considering entering the market in Fire Island, specifically through the purchase of a single family home and exploiting the summer rental market.

If you are buying a property under market you are likely either (a) lucky (not a sustainable model; (b) exploiting someone (not a sustainable model) or (c) in for a big surprise in terms of what you thought you were buying (not a sustainable model).  

While each case stands on it's own merit, it may be beneficial to exploit the deduction at the higher tax rate in 2017 - if it is feasible and makes sense.

Look for what makes your community tick and exploit it.  

Take advantage of rushing prices but be prepared to exploit falling prices too.