I hire one guy with years of experience operating excavators from large to small. He is now completely independent, has his own mini-ex and small dump truck. He has access to a tri-axle for hauling stone and other things like roller as warranted.
IIRC, it cost me $80/hr for the mini-ex, $40/hr for the operator and so on. So basically $120/hour to get things done by a professional who is efficient at operating his machine(s).
Just had a torrential rainstorm(s) damage much of my ditches, culvert area and driveway(s) at my main house/barn and adjacent 'for sale' flip house. I had just last summer/fall built my implement shed close to my ditch/woods line and had I gone closer to the ditch/woods I would likely have had sustained damage to my shed's poured Alaskan slab foundation. Fortunately my contractor strongly urged me to place the shed and two aprons further from the woods for better access turning in and out with the tractor and list of implements shown in my signature.
Now I'm likely going to have to spend $10K or more on re-excavating a lot of the ditches and driveway damage around my 30' deep 50' wide barn with attached enclosed boat bay and above apartment with rear entry workshop and extra 'garage bay' for overflow storage.
Again, I consider myself fortunate to have had an excavator who did the work for the barn and carved it out of wooded land that I and my son and one of his friends cleared of dense trees. The excavator knows the land in my area and dug a 14' deep curtain drain around the rear and one side of the barn. Had he not done so then, before Irene and Sandy hit the Northeast, I would likely have uncontrollable flooding at my boat bay and adjacent 3 garage bays at the lower level of the barn.
As it is now I have to redo much of what I had to redo once Irene and Sandy wreaked havoc in our area - bring in larger stone to keep the ditches from having their existing stone washed downhill to the end of my driveway. I lost count at 70 bucket loads in my DK-40, which I hauled up my 400' uphill drive to make a foundation for my Shelter Logic storage building. The constant haul was a total PITA after about 10 loads, but I needed it done and didn't want to pay at the time to have someone else do it, and I had a machine on hand, though slow to get it done.
My point in detailing this out to you is an experienced conscientious person who has years of local terrain knowledge can help immensely in deciding how and where and when to do certain thing like ditching, drainage pipe sizing, etc.
I'm always the final decision maker, but I listen to and ask questions and make suggestions and require certain things of those working with/for me.
Currently we've decide to have the excavator bring in bigger rock to create a catch basin above where the various washouts have occurred over the years. We've learned from the damage done by the storms what works well and what needs revision.
Fighting mother nature is often a losing battle, but having done battle with her for the last 35 years here tells me we're gaining on it overall.
So conclusion for me is; learn from those with existing experience in your local area, chances are they've encountered it all over their years doing battle and you can save on trying to reinvent the wheel.
And the thinking is if one has too high expectations one is most likely to experience disappointment. This cognitive behavioral therapy caveat holds true with your desire to get the 'perfect cut' on your fields grass. Are you going to be creating a home golf course, something the ultra-wealthy in my neighborhood knock themselves out doing, or can you get by with a nicely mowed field which looks good from a short distance?
You can have either, but at what point is the cost beyond belief, or nearly unobtainable?
I saw what Kioti offers yesterday at my dealer's lot for a rear finish mower. It did look to be a woods rebrand, and had 4 gauge wheels, one on each corner. But will it produce a clean enough cut for a manicured look field? I think not likely as Woodchuckdad and IT have said - there are good, better, and ridiculously priced mowers to tow behind a tractor available. You have to chose what will work best for you and then accept the decision's result. Hopefully it will be close enough to your expectations for you to be satisfied with the end result. Few things in life are even close to perfect.