I use to pull a 12' 5 gang reel mower with a 2wd 17 HP Kubota back in the early 80's to mow the fairways at the golf course ...
But for my situation it comes down to how much money do I want to spend ... ? I'm the kinda guy that just because I have the money, doesn't mean I gotta spend it ... It has to make sense to ME!
I was frustrated earlier trying to find a no computer or emissions 50-65 HP tractor, light enough to fit on my 5K Lb net trailer, under $15K (so - 2 WD, no loader or cab) so my local dealer who had been looking for a few months, said maybe look at bigger, and if it needed work in town he would come fetch it for $4.50 a mile, I could drive it the 6 miles home when fixed ... So I started looking ... 90 -120 HP and 15' - 20' flex/batwings ... WOW those mowers were more money than the 30-50 year old tractors I was looking at! They also are more maintenance ... And burning 7-9 gallons an hour ... For my 14 acres ... I decided to just be patient, the money was just adding up in the bank every week ...
This Kubota I got, I had seen back in the spring, but it was only an "L" ... A CUT (too small!) ... I was looking for a Utility as my two "must have" priorities were big tires for ride comfort, and as much PTO HP I could get in a tractor under 5K Lbs ... But, I saw it again on tractor house, I clicked on the link, I knew why it was still for sale, most people want a loader on that size of tractor! It just barely had the HP I wanted, and after researching the tires on it, I discovered that the "Grand" series of the "L" has a heavier frame/transmission, and bigger tires, these are twice the height of my SCUT 52" vs 26", so I decided to give it a try, I was able to talk the dealer down a bit ... While it had a cab, it was still under the weight limit, and the previous week in the July HEAT, the A/C went out on my new Kenworth semi-truck ... 4 miserable days, finally put my foot down in Dallas, TX that I was NOT going to deliver the load the San Antonio until it was fixed! I figured A/C in a tractor would be a nice change for mowing ...

And it turned out I was right ... I just picked up the 90" finish mower and it's a good fit for both the tractor and my terrain, no scalping, but gets quite a lot more done than my 56" cut Bush Hog I was using before ...