Much smaller scale here as I only maintain 62 acres, but it is in GA, has pine trees, and lots of red clay and sand. I built my perimeter and interior roads which cover somewhere around 1.5 miles in total. We also have two lakes and some elevation change. I've been through a bunch of equipment trying to find the best setup for my use.
I've tried numerous sized tractors, we've owned a Deere 310k backhoe, and mini excavators. What I've settled on is a 60hp tractor with hydrostatic drive. Its a Kioti, but approximate size of a Deere 4 series. I've owned larger frame and higher horsepower tractors but the issue I always face is fitting through the woods. They just become too big when you have to maneuver or get into the woods with them. While they certainly have more power and more capability, they do have some downsides.
With ponds and trees, we area always needing to dig something. A large backhoe like a 310k is great, but I've found an excavator to be more useful. Much less ground pressure on tracks than 4 tires. I can get into softer ground areas without sinking. The 310k is around 15,000 lbs and my excavator is approximately 12,500 lbs.
Reading the posts, and looking at your pictures, and then trying to put myself into your shoes, I would probably be looking at something like this:
> 100hp to 150hp range tractor - geared transmission - with removable front loader - for pulling heavier equipment for road work and material moving. I would add as many rear hydraulic ports as possible. 3 or 4 depending on what tractor supports. Add hydraulic top/tilt links which are invaluable for crowing roads with a tractor.
> 50hp to 60hp range tractor - hydrostatic transmission - with/without loader - for mowing around buildings, fences, tighter access areas, etc. Also, for getting into the woods, and for easier transport on smaller trailers.
> Excavator - with 4 way or 6 way blade - with thumb and dedicated secondary aux hydraulic lines for high flow item like brush cutter or mulcher. Mine is a 5.5 ton unit, but for your property you may want way bigger. That said, you would be surprised what you can accomplish with only a 5 to 8 ton machine.
> Implements
* 6 to 10 foot wide brush mower - depends on how large your open areas are and how narrow your roads are. If you are doing a lot of cutting on fire breaks and roads through woods, a bat wing or large mower might not make as much sense as someone maintaining a pasture. For me, a 7' mower is too large for many areas and I end up hanging it on trees/posts, etc. I stuck with 6'. Your need will be unique to you.
* Land Plane / Grader - May make sense. I have one but rarely use it. Once my roads were formed and grass began to fill in, I find that I mostly only need to cut them to maintain them. If you pull the land plane over those roads, just like a disc/harrow, you may just be inducing new errosion.
* Harrow/Disc - For cutting new fire breaks, and major rework of roads and firebreaks.
* Blade and Box Blade - I have both and use both. A box blade is great for dragging material and moving material, but many tasks can also benefit from an angle blade. Road crowning with an angle blade and top/tilt links on a tractor is a joy. Easy to set your angles and just drive making small adjustments while you go.
* Front Tractor Mower or Excavator Brush Cutter - For tree trimming and maintenance of road edges, these are invaluable. No matter how many times I mow our roads, we constantly have brush growing between the trees that extends out into the roads. About twice a year, I mount the front mower and drive through cleaning them up. Also useful for pond bank maintenance. I've been using a tractor mount version with pto driven hydraulics, but just purchased an excavator model to also supplement harder to reach areas.
Also, if I were to scale up to what you are doing I would not be without a Dump trailer or dump truck - nothing sucks more than moving dirt one tractor scoop at a time. Even on only 62 acres, it takes forever to move any amount of material from one side to the other.
I added some pictures for reference. Just showing property type, road types, material type, etc. Realizing my experience isn't exactly transferable but maybe it adds some additional thinking points to the mix. Good luck!