Lineman,
I suspect but don’t know for a fact that the Illinois trailer laws influence some of the decisions on towing vs hauling.
Figure a tractor the size of a John Deere 50 or 60 or Farmall M at around 5000 - 6000 lbs depending on how they are weighted plus 2 or 3 bottom plow is another 700 - 1000 lbs. This weight would require minimum of 10K trailer and 3/4 or 1 ton tow vehicle and most likely gooseneck or 5 th wheel.
In this area there has been a significant increase in roaming road side scale an inspection stations targeting over weight trailers, I uninspected trailers, etc.
In Illinois any trailer over 5K required yearly inspection or at that was the rules a few years ago. Plus license plates, registration, insurance, etc.
Towing could be accomplished with 1/2 ton pickup so significantly less cost and hassle for something you do a couple of times a year.
Not saying one way is better than the other but I can certainly understand why it is being done by old timers that know what they are doing.
I cringe more at people pulling tandem anhydrous nurse tanks behind a pickup at 20 plus MPH and that is done here every spring and fall.