I maintain about that much land. Around the house, I use a zero turn. Before that, I had a riding mower. Both did a nice job of making the lawn look great. An acre or two of really nice a lawn around the house is plenty. I also have a 7 foot finish mower that does a nice job when mowing straight lines or gentle curves, but it's really not all that great for getting in and around the trees, or close to the house and fences. It also doesn't leave anywhere near as nice of a finish as my zero turn does. I've had it parked and off to the side for several years now and will probably sell it one of these days. To maintain my pastures, trails and around my pond, I pull a 6 foot rotary cutter, also called a bush hog by many with a 37 hp open station 4x4 tractor. It's gets the job done, but it's probably borderline on having enough power. I will mow stuff that's over my hood with it, but I have to be in my lowest gear to do this. On foot high material, I can cruise along in mid range 2nd gear, which is my fastest speed for mowing. I will still downshift when I hit some really thick stuff, or have to go up a steep hill. If I was to do it over again, I would get 45 hp, but when I do buy my next tractor, I'm going for something in the 80hp range or more with a cab and I will pull a 15 foot batwing. There are just too many other things that I can be doing if I spent less time mowing pastures.
Based on what you have asked, I would pass on the finish mower and get a riding mower. Changing from rotary cutter to finish mower isn't something you want to do all the time. Once my rotary cutter is hooked up to my tractor, I rarely take it off and when I do, I REALLY think about it first and try to come up with any other option to not have to take it off. The older your stuff becomes, the more effort it takes to hook it up.
Get a 40hp or bigger tractor and a good quality 6 foot rotary cutter.
