Its been a while so I thought I would update. I switched form the sickle mower to a PZ170 drum mower. Cuts better in the wind and does some conditioning. It does take longer as it is not as wide. I also now have a Kabota rotary rake - what an upgrade from the side roller. However I am now done with horses, so this is probably my last hay year and I will just flail the pastures or let someone else cut it. I am getting old and the fun is mostly gone.
So tips to look into . Depending on your state set up a personal LLC. In CO its easy (25$) I think with $10 year renewal. Then file a SCH F federal tax form and deprecate all of your equipment. You also get to deduct you fuel, parts, repairs, chemicals, fertilizer, seeds, etc. I used H&R tax software to set it up with a bit of help from thier help line. Once doe it easy as the tax software tracks things from year to year. You will find it is a huge help come tax time with the deductions. Basically I save enough in taxes to pay for the equipment the year I bought it. This is all above board and legal - Only once did I have to send the Feds/State additional information (receipts for major tractor repairs) I guess they the call that a mail audit. Once sent everything was fine . I only did between 250 and 500 bales (weed free custom grass horse hay) a year too, sometimes less. The year I got the question was a drought year where I maybe sold 50 bales, but the tractor needed a new fuel injection rack - ending with a huge farm loss on the tax form.
BTW - having an LLC limits (protects) your personal other property in case something goes wrong - at least in CO Be sure to consult with a legal person on this depending on where you live
Something to look into depending on your situation.