Quote from @Jeff Brogan: I would hire a trusted expert to get you real numbers, someone that does it in that area all the time (rents out properties/property management). 

With expert guidance, tailored training, and a supportive community that will align you with the tools you need to fast-track your success and avoid common pitfalls.

Like Lisa said, the only place I'm aware of this being a thing is in Ellicottville, but I am not an expert on that market.

While it’s not impossible to close in mid December and still meet all requirements of the STR loophole, it will be extremely difficult due to the nature of hitting 150 hours, having it rented for 15 days or greater and having the avg stay be no greater than 7 days and not a decimal more.

It is extremely difficult for your tax preparer to know if what you give them is right without a balance sheet unless they dig into each transaction which will be very costly.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.PM us if you’d like to discuss this logical approach in greater detail!

I would have to call someone that is extremely motivated to sell and willing to accept any offer despite what they had listed to accept the offer on the 1st call. 

That's extremely difficult :(The good news is, it sounds like you have equity in your property.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.PM us if you’d like to discuss this logical approach in greater detail!

For example at a typical showing, buyers like to have an expert with them who can help really evaluate a property, not just a door-opener as you seem to think will work.