This gets rid of bad apples and also lets the procrastinators know that waiting to pay rent to me  is not a good idea and is very costly with additional fees and all.  

Listening to YouTube big shots that have great advice on professional ways to handle problematic guests ( most are great but everyone will get bad apples), staying at the property when you have an open window of time and actually get the guest experience (this is critical), and looking at your click thru and conversion rates to get a good baseline.There is way more work to running an STR than a LTR.

They built a pole barn structure, air conditioned it, strung up some lights and trendy decor and host baby showers or weddings almost every weekend. 

Are we comparing bacon to Christmas trees, to apples, to venus fly traps, to tomatoes, to grapes, to kelp? 

And later on, take advantage of the 1.1 acres and put up Yurt/ Dome / Tiny house etc as a glamping setup.Pictures:The 3d model Front view ( The barn with loft)Right view (Barn, Kitchen and .. the back part I lovingly call, the pizza) == also, what i plan to do with it.back view ...Current view and the Planned renovation viewThe left side view Location:115 miles from NYC ( 140 minutes)12 miles from Woodstock and Hunter ski mountain. ( 25 mins)8 miles to HITs Saugerties (15 mins)25 minutes to Hudson.The cities I have just mentioned are the TOP Airbnb locations in Hudson Valley/ Catskills as listed below. ( I wrote a scraper program to get all the Airbnb data) city Total number of homes on airbnb Total number_of_reviews average number of reviews Woodstock 141 7720 54.75177305 Hudson 142 6636 46.73239437 Phoenicia 57 3458 60.66666667 Saugerties 125 2983 23.864 New Paltz 66 2237 33.89393939 Beacon 54 1860 34.44444444 Catskill 45 1761 39.13333333 Hunter 79 1445 18.29113924 Rhinebeck 48 1413 29.4375 Kingston 62 1380 22.25806452 Kerhonkson 32 1293 40.40625 Accord 29 1275 43.96551724 High Falls 20 1122 56.1 Tivoli 14 940 67.14285714 Olivebridge 13 886 68.15384615 Rosendale 16 834 52.125 Cold Spring 19 813 42.78947368 Athens 11 803 73 Mount Tremper 23 762 33.13043478 Stone Ridge 17 742 43.64705882 Windham 60 740 12.33333333 Germantown 34 718 21.11764706

If you bake me an apple pie and ask if its the best I ever had in life and I say, "its cool but can use different crusts", ' I'm not being mean.

Above are just hypotheticals, but they bring to light the point, which is, evaluating opportunities requires apples to apples comparisons. 

After all that some get the AHA moment that this business is not easy while others still think that its picking an apple from a tree. 

There's always some bad apples in any bunch but for vast majority, it's a win-win. 

That's like buying Apple stock and calling yourself a market expert.That really depends on when you purchased Apple stock ... when it was $22/share, folks had the same opinion of it as you hear about sub-30K houses/pigs.