expense deductibility

[99ugh]

Hi - I am preparing to file for 2019 using Turbo Tax & I have a complicated question. I file Schedule C as a sole proprietor (freelance writer). In the past I have also filed a Farm Income form but I stopped doing this when the interest on my rural property land sale contract dropped to a low figure. I now own the land free and clear. An adjoining landowner helps me with the place (I live in a metro area 300 miles away) by cutting hay and gradually improving the pasture; he also gets firewood. I need this activity to qualify for an ultra low Farm & Forest property tax rate; otherwise I would have to pay staggeringly more, thousands of dollars versus a nominal sum. But the farm has never generated income as such, and now I am paying this future neighbor some real money (approx. $6,000 in 2019) in a 3-yr project to put a 1,000 ft. road into the place. How should I go about expensing this stuff, if I can?

[DavidS127]

The road is a "land improvement" asset.  As far as deducting the cost, the question is whether you are actually engaged in the business of farming.  If you are, you can depreciate the land improvement.  If you are not (see the section of IRS Publication 225 Not-for-Profit Farming at this link), it is an investment in personal property that increases your "cost basis" in that property.