It is possible to get too large of a tractor. A tractor is too large if it can't maneuver well enough to easily get into the places where you are working. Having to make frequent multi-point turns to maneuver around gets very old very quickly.
I read the entire thread including the numerous tangents that got well off topic. The OP has 58 acres. Most of what he plans to do is run a rotary mower to keep the weeds knocked down on 28 acres of open land at most a few times per year, maintain a several hundred yard long gravel driveway, and take a few trees down on the 30 acres of woods. Appropriate implements for that would be a 6-8' rotary cutter, a 6' box blade, and a 6-8' straight blade. I would not recommend a drawn cutter unless your field is completely open and has no obstacles. I would not want to run one up and down a trail either. That pretty much limits you to a 6' cutter with a larger compact as they can't really handle an 8' 3 point cutter due to weight, you would have to get a full sized utility tractor to run one. Personally I would get the 6' cutter as it will take roughly 15 hours to cut the 28 acres of fields, which will be done at most a few times per year. A 6'er has one gearbox and costs $2-3k for a decent one, an 8' unit has three gearboxes and costs about five grand more. Unless the OP wants to run an 8' cutter, a larger compact such as a Deere 4 series or larger Kubota L/MX would work fine. I wouldn't recommend going larger than the smallest full-sized utility tractors (e.g. 3 cylinder Deere 5E, Kubota M60). I also wouldn't see much of a benefit of much more than about 50 HP here either. If you do get a full sized utility tractor, none of those tasks require a MFWD machine. MFWD is not needed for running a rotary cutter. A 2WD utility will also pull around a 6' box blade and overflow it without even knowing it's back there.
The full sized utility tractors will have a gear transmission, weight quite a bit more, often have fewer electronic features, generally be less expensive, and pull ground-engaging implements with more authority (due to the heavier weight.) However, an MFWD full sized utility tractor will have a turning radius at least half again as wide as a larger compact (or a 2WD full sized utility tractor, which is about as maneuverable as a large compact.) Often people will get the full sized tractor for property maintenance if they can drive a clutch, have enough area to maneuver the machine, and performance in pulling ground-engaging implements is important. People will often get the larger compacts if they can't drive a clutch, have small areas the tractor has to fit into, and don't do a lot of ground-engaging work. I personally prefer gear transmissions particularly for any sort of cutting/mowing and ground-engaging work. They are not hard to operate with a little practice and there is no issue with using one with a loader, even a regular manual without a hydraulic reverser.
Regardless of what size tractor you get, I recommend you get fluid-filled ag tires rather than industrial tires. The traction difference is quite noticeable.
Cabbed tractors are bulky and not a good fit for the woods as a result, I would advise the OP to get an open station tractor.
