I bought a tractor,2 backhoes, dump trailer, enclosed trailer, flatbed trailer, lots of tools, roota rooter, commercial steam cleaner, etc.

With the information you provided, I think two of them does not apply to you ( de minimis safe harbor for 2,500 or 5000 (Hoping the expense was higher than 2500 ) and routine maintenance safe harbor- does not apply to you).The third one might apply, since we do not have info on your basis, please look into the Safe harbor for small taxpayers:You can deduct improvement on the property does not exceed the lesser of(1) 2% of the eligible building property’s unadjusted basis or(2) $10,000 Also, we should consider court cases over the years that have allowed few of the expenses related to the driveway to expense rather than capitalize. these are what court decided on few of them:Per court case, these expenditures can be deducted as repair and maintenance for the driveway, parking lots etc:1) recrowning and resurfacing with the same materials as in the road without lengthening or widening or changing basic construction2) constructing logging road on adjacent state property including repairs to tractor used in constructing the road3) patching asphalt steel mill driveway4) resurfacing a three-year-old parking lot to restore it to its original condition after construction.

"  Witnesseth, that the party of the first part, in consideration of Five-hundred Dollars ($500.00) lawful money of the United States, paid by the party of the second part, does hereby grant and release unto the party of the second part, their heirs and distributes and assigns forever,ALL THAT TRACT OR PARCEL OF LAND, situate in the City of (XYZ), County of (ABC) and State of New York, being part of Lot No. (00), Township (00), Range (0) of the (ABC) Company's Survey and further distinguished as Subdivision Lot No. (0) as shown on map filed in County Clerk's Office under Cover No.( 0).Together with the appurtenances and all the estate and rights of the party of the first part in and to said premises.To have and to hold the premises herein granted unto the parties of the second part, his heirs and distributes and assigns forever.And the party of the first part covenants as follows:First, that the party of the first part is seized of said premises in fee simple, and has good right to convey the same;Second, that the parties of the second part shall quietly enjoy said premises;Third, that the party of the first part will forever WARRANT the title to said premises;Fourth, that this conveyance is made subject to the trust fund provisions of section thirteen of the lien law.That this Conveyance is not all or substantially all of the property of the party of the first part and is made in the regular course of business actually conducted by the party of the first part.In Witness Whereof, the party of the first part has hereunto set his hand and seal the day and year first above written   "

Sitting up there in the tractor during planting and harvest season listening to music and steering between the crops.A couple of hundred acres under the plow, deer and pheasants dashing around your fields.Maybe grow peas, or corn, whatever.Have a personal garden for your families food, eat outside on the pic-nick table in the summer.USDA does farm loans.Another Non-W2 I have seen people do is owning a package delivery route and delivery truck. 

That's not the case, since you often need to get to both sides of a fence to maintain it, and that usually means a pickup or tractor.

This is America, but I need a license to fly an airplane, a license to drive a car, a different license to drive a tractor trailer, etc.

And luckily I had moved my tractor and implements off site.

When doing it all yourself, having the right equipment makes a world of difference and we have reinvested a LOT of money into tools, trucks, dump truck, tractor, backhoe, mudmixer, scaffolding, trailers, etc...I'm extremely fortunate to have a 3 man crew that is very efficient and we've learned to "dance" together on the job.

Properties should be in the same tract, or you need to know how to adjust them for condition, age, view, upgrades, amenities, and 20 other things.You need sale date, value, upgrades... 

Plan on bringing in our tractor to clean house.