Fluctuation, zoning, REzoning, demand, topographical data, etc...To give you simple examples as to how big of a spread between one deed transfer and the next; I have seen land that was bought for 1.25M only to be resold for 80K, a multiparcel that previous owner bought for 500K resold for 5K, etc...Bottom line, in REI land is by far the most rewarding yet the most devastating of investments; and, since you're new to real estate, I think it's best to read about it and do extensive research first and foremost.

I am currently in the process of filing my 2015 tax return (extension) where I can remove those expenses to increase that year's self-employment income, but that income would be taxed at the 28% bracket so not sure if it's worth it. 

It is very important to file an extension by the March 15 or April 15 deadline, depending on whether you are a business or individual, because not filing an extension will result in a 5% per month for failure to file penalty, but it is equally important not to file a full tax return if your exchange is not completed by the applicable filing dates referenced above.    

We have discussed Airbnb but not have researched it extensively in regards to where that's working besides the attractions here.  

A little bit about myself...I was born and raised in Westchester, NY (about 45 minutes north of Manhattan) and currently have a career in Interior Design & Textile Sales, with an extensive background in residential design & construction.

The HML lenders add on increasing costs for any extensions because the most money for them is typically made on the points charged on origination.

It does not require a consultant and will be a faster process so you shouldn't have to pay extension fees.  

Thanks for the extensive and comprehensive list

However, this only occurs when the buyer has extensive real estate knowledge, extensive experience, and a large network of FIRST tier contacts.  

On a spreadsheet it's usually cheaper to go via hard money lender, if you can avoid their extension fees.