I've tried to stay out of this. But oh well. Golf course groundskeeper unt uh. They see the same grass week in and week out. plus it would be sacrilige if it was ever to get over 2" high. Now a property maintenance company maybe, especially if they offer their services to rural property owners. Rural feild mowing services, a definite contact, although they are gowing to tell you they can faster and better than you can. You will probably get some good advice on what euipment they use, how long it takes and what to avoid.
I mow grass and feilds for other people. Not full time, as to call it a real business. But as word of mouth got around, the dang phone won't stop ringing. Until this spring I have mainly been using a twenty two year old 34.5 horse power 4X4 Kubota. These machines ( L345DT ) still hold their value if maintained Local dealer offered $8000 purchase for tractor with @ 1600 hrs, and $10,000 if it included the backhoe. I turned him down, told she still had another twenty years in her as my back up tractor. Mind you this is a machine that does not have a synchronised transmission and almost non existant power steering. I have downsized this year not so much in horsepower (34.5 to 29), but also in frame size for maneauverability and stability on slopes. Just purchased a New Holland TC29, with synchronised manual transmission (simply my preference). Also includes 4X4, calcium filled rear industrial tires (R4's) and a heavier duty Woods front end Loader. Their is also a Woods 7500 backhoe, once again that was my preference. A tractor of that size would probably be ideal for your property. With a hydrostatic transmission they are very easy to learn how to operate, and make great first time tractors, with enough power for your size of property. Kubota 2710, 2910, or even going into the next larger frame 3010, would probably also be a good match for your property. as well as the John Deere 4310. If you can handle a manual transmission allthree of these manufacturers offer economy versions with relative horsepower cheaper. I would make sure they are equipped with a synchrnised transmission and live PTO. Out side of the big 3, you might look at Kioti's DK series or the Long Landtrac's. Both seem to be well made from up and comming companys
Now lets talk about mowers. As I said before I mow. Everything from 1 acre lots to 13.5 acre estate, as well as feild mowing. For the latter generally if the grass is higher than 1 foot and may or may not contain saplings, rocks and or ruts its my 5 foot Brush hog. For some of my jobs that i have been doing for a long time ( know where all the surprizes are) I'll use the 6 foot 3PT finish mower. these also get done more often. For lawns and esate mowing, its the 3PT finish mower 100% of the time. Also I don't do the trim mowing. For your place. Not knowing what you have for obstacles I'm goind to recomend a 5 or 6 foot 3PT finish mower for the lawns. For the feilds a 5 foot brush hog. Later after you get all of the hazards removed or memorized from your feilds you might try the finish mower, just remember you'll be out there more often. Also no less than 27 horsepower, 4X4, with power steering.
Now lets talk about older tractors. In a word most are finicky. You had best be fairly mechanical, as they like constant attention. Controls and steering can be tempermental. And unless you have a lot of experiance, there can be a considerable danger factor involved also.
Well there I tried to stay out of it. But OH WELL!