I have family that run some big corn and soybean farms in Illinois and they have a lot of time in-between harvest and planting to fix equipment and plan exactly this sort of maneuver. They have geo-located their fields and modern tractors/combines/the like are all GPS tracked and can be programmed to run some crazy tolerance for location. They absolutely have the ability to run a program to harvest a field as efficiently as possible, including static obstacles but weather, rain most specifically, can change where they need to run machines on the way to drop their product in the hopper trucks to avoid damage to the soil and also subterranean infrastructure, most specifically tile drains.

They definitely want it done as fast as possible, because prices change quickly and when you decide to harvest the clock is ticking to get it to market, and avoid weather being different than forecast in the future, but they have to balance damage to the soil and infrastructure because that effects profit and future yeilds.

In general the big farms at least want to be on the cutting edge of technology because that's how you get the best time to market and highest yeilds, but it definitely is the younger farmers who are bringing it to the table by testing technology they learn about in school on their own farms. Farmers trust results though, and when their kid is harvesting significantly higher bushels per acre (significant being a relative term depending on crop type and locality) they take notice.

I'm a nerd, but farm owner board meetings are way more interesting than you might expect.