I hire mine out because the pasture is hilly and I don’t like driving on the hills particularly. And also - my grass is THICK and I am certain it would shut down my 22 HP tractor. My neighbor who is now deceased used to do it for me. I think I paid him $200 and a pan of banana pudding with whipped cream on top. He had a bigger tractor than I have and it took him a day and a half to do all 15 acres. Slow going in tall thick grass.
The rates have gone up and I have a guy that mows it for me - $500. He has a huge tractor and a 15 foot batwing mower and can do it in around 2 to 3 hours. He works out of town so it is hard to get him sometimes and even with that big tractor the grass in the bottom lands will almost choke the tractor out. He is close enough so that he just rides the tractor over - no hauling involved.
One year when he was not available I hired somebody else. His Kubota was bigger than my tractor but it was not a big tractor. When he came over to my place to price the job I questioned if his tractor was large enough because I told him that grass was tough. He assured me it was fine for the job. He quoted me either $200 or $300 - I can’t remember which. He started mowing in July. He still had not mowed the whole pasture by October. It was crazy. At the end I could have mowed a larger patch than he did with my riding mower. Everyday he would drive the tractor over with his truck and trailer. And drive it home that night. And park on my water meter although I asked him multiple times not to do that. So I was eager to pay him and see the end of him. This went on for months. Finally he threw in the towel, i paid him and have never heard from him again.
And a long time ago I traded out free mowing for “you take the hay”. I did not have cross fencing at the time so I was adamant about them keeping the gate closed. I heard from said nosy neighbor who sat outside in his chair all day - they were leaving the gate open since I was not around to keep an eye on things. And they round baled and I thought they were never going to pick the bales up. And the other thing - it was in their best interest to let the grass get tall before mowing. My one horse gets sores on her legs from tall wet grass so that wasn’t working for me either. Gonna stick with the guy that can get it done!
I do wish I had a bushhog to keep the pasture areas around the barn mowed on a more regular basis. But I don’t know how to do PTO, don’t want to deal with hooking it up and no where to put a bushhog that is under cover and accessible and not in the way.