Upstate New York Investment Property Turnaround

[Jesse Bull]

I bought a house in Woodstock, NY about 5 years ago.  It was always meant to be a weekend home whose costs I could partly cover through AirBnB...I wasn't as thoughtful or concerned about the annual loss in the early years but now realize it's taking away from my efforts to build wealth - though I don't regret the great times I've spent there with friends over the years.  It's a great quirky house on 26 acres.  I've had about 150 rentals over the 5 years and great reviews on AirBnB.  Generating about $35k-$40k in rental income a year. But the taxes are really high in the area ($15k per year) not to mention high gas and electric bills.  All-in, I'm still losing $20k a year on this place.  I see a path to maybe close the gap by $10k by being smarter on costs, increasing rental pricing, etc.  But struggling to fully close the gap. 

While it may be that I need to just sell the property and reinvest with a real strategy now that this is a focus, I'd love any creative ideas on how to get more value out of this property.  2 thoughts I had: (1) trying to negotiate the taxes down - any tips from people who have been successful here?  (2) the land is actually already on 2 separate tax lots.  Maybe I should consider selling the vacant land on 10-acre lot..or even developing it with a small tiny home or something and selling that.  

Thanks for any thoughts on specific tactics or creative thinking here!