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Update: Off topic. Tractor vs. Skid Steer

I see you are in VA. What kind of maintenance? What' the widest cutter you are going to run? I bet you will need to spray.?? How about fertilizing and planting? discing? Aerating. Where I live if you dont spray or run a cutter in 3 years you will have 2 inch diameter sweet gums and persimmons-not to mention blackberries chest high.

My advice is to clean it up good first. Rent/buy whatever suits you. Dozers and skid steers excel here. A lot of times you can buy a piece of equip. at an auction and break even or make money when done with it. Then get a MFWD with a front end loader with a 3 pt and PTO for maintenance.
I will be maintaining 7 cleared acres, just keeping it mowed. It was farmed until the last growing season. The previous owner of the property had leased it to a local farmer who grew corn. We will be building a house on part of the cleared acreage. We have not decided what we are going to do with the balance of the cleared land. I do know WE will not be farming it. So, the maintenance will be mowing the acreage, keeping the long gravel driveway and trails dressed up. I also want to build a rifle range. I would get a 15 ft wide brush hog for mowing the acreage. For the lawns around the houses, I have a zero-turn mower. Spraying -yes; Fertilizing - lawns yes; discing -no; tilling a small patch for a garden. Maybe some other tasks. I can rent attachments for the infrequent or one time tasks.

PopCharlie
 
I like skid steers. I dug my basement with a skidsteer. Later I built my campground, mostly with a skidsteer. Today, I still have the skidsteer' along with a D-4 cat and a 3 ton Kubota excavator.. Only the excavator is new(ish). If I was to buy another new piece of equipment, I honestly would have trouble deciding between a skid steer and a tractor. WH
 
I will be maintaining 7 cleared acres, just keeping it mowed. It was farmed until the last growing season. The previous owner of the property had leased it to a local farmer who grew corn. We will be building a house on part of the cleared acreage. We have not decided what we are going to do with the balance of the cleared land. I do know WE will not be farming it. So, the maintenance will be mowing the acreage, keeping the long gravel driveway and trails dressed up. I also want to build a rifle range. I would get a 15 ft wide brush hog for mowing the acreage. For the lawns around the houses, I have a zero-turn mower. Spraying -yes; Fertilizing - lawns yes; discing -no; tilling a small patch for a garden. Maybe some other tasks. I can rent attachments for the infrequent or one time tasks.

PopCharlie
just like rifles....one cal. cant do it all...
 
I have access to a lot of equipment. I like the idea that Adam had on the wheeled front end loader, they can get a lot done. Get a big zero turn mower with a big high back chair-seat to do your mowing, and you can thank me later.
 
I have 20 acres and none was cleared when I bought it so I have been clearing as able to for 40 years.
I bought a JD 4320 compact utility tractor with a back hoe attachment and 6 ft rotary mower( bush hog)
we now have about 6-8 cleared and into pasture for our horses.
I still have trees to clear and while I could get by with the 448 hoe attachment I bought with the
tractor It has no reach and is under powered.
As far as mowing it is fine. and the loader is able to lift 1700+ Lbs.
All equipment is a compromise in my opinion unless you have deep pockets.
A wheeled skid steer is not much good off pavment so I would get tracks or nothing.
A too large tractor can be awkward around buildings but the power and stablity and traction is
great when cutting trails.
I found a still solid JD 310SG back hoe in 2016 and it is actualy fun to dig out oak stumps with it
after using the how attachment on my small (48HP) tractor.
My vote is get a 50 HP tractor and use it until you figure out what would be a better piece for what you need to accomplish and buy a GOOD used piece with low hours and bot abused.
 
I will be maintaining 7 cleared acres, just keeping it mowed. It was farmed until the last growing season. The previous owner of the property had leased it to a local farmer who grew corn. We will be building a house on part of the cleared acreage. We have not decided what we are going to do with the balance of the cleared land. I do know WE will not be farming it. So, the maintenance will be mowing the acreage, keeping the long gravel driveway and trails dressed up. I also want to build a rifle range. I would get a 15 ft wide brush hog for mowing the acreage. For the lawns around the houses, I have a zero-turn mower. Spraying -yes; Fertilizing - lawns yes; discing -no; tilling a small patch for a garden. Maybe some other tasks. I can rent attachments for the infrequent or one time tasks.

PopCharlie
100% a tractor job. 50-60 hp, mechanical front wheel drive, loader. If you are getting any 3 point attachments, get a quick hitch. Your back will appreciate it.
 
Get both if you can. That said, a tractor will do everything a skid steer will and most things better. Those skids are tough to beat if you are moving dirt. As far as money, You’re going to have 50-60K+ in a good sized skid and still need attachments, not cheap. If you want to hit the easy button (and spend some money) 50 horse Kubota is hard to beat. All the attachments available, dealer support everywhere. If you want to do it cheapish and are kinda handy, a 30 or 40 series Deere with a loader would do.
 
Get both if you can. That said, a tractor will do everything a skid steer will and most things better. Those skids are tough to beat if you are moving dirt. As far as money, You’re going to have 50-60K+ in a good sized skid and still need attachments, not cheap. If you want to hit the easy button (and spend some money) 50 horse Kubota is hard to beat. All the attachments available, dealer support everywhere. If you want to do it cheapish and are kinda handy, a 30 or 40 series Deere with a loader would do.
Get 4wd and as much horsepower as you can afford. Air conditioned cabs are nice if you can afford it.

If you plan on doing a lot of clearing, I would prefer a track loader with a 4 in 1 bucket over a skidsteer or a tractor.

Doing finish work in tight quarters, a skid-steer or smaller tractor is easier to handle.
 
Friends of mine own a 16,000 acre working cattle ranch. The tractors are only used in the wheat and hay fields. Three skids steers handle everything around the ranch house and working pens. The shredding and mulching attachments make short work of vegetation and small trees.
 
CTL: compact track loader!
Don’t buy a skid steer, they get stuck in wet conditions and don’t have the push that tracks do. Either buy or lease long term. Get the biggest one you can, 90 hp min.
 
My vote would be to carefully select someone with a trackhoe with a thumb, who has a good reputation in your area to do the land clearing. It will be done faster than you can do it yourself, and the trees and brush should have the dirt shaken off and piled nicely to burn. Anyone in the business will probably also have a dozer with a root rake to make things really nice. And is should be cheaper than heavy equipment rental combined with inexperience. Also, anything you own can and will break/have problems that can be expensive. The only thing good about a rental is that if it breaks, they will usually swap it out of they can't quickly fix it. Odds are someone inexperienced will inadvertently break something.

A 15' bushog is good for big, level areas. If the ground is uneven they will scalp. Over the years I got real attached to the Bush hog brand 10'. It is tough and will take down almost anything you can back it over. Plus it only has two sets of blades, while a 15' will have three. It will take a minimum of 100 PTO horsepower to efficiently run a 10' bush hog, and more for a 15'. For the areas you are describing a 7' 3pt hitch bush hog will do fine. Again, over the years I got attached to the Hardee brand because they are tough, reliable, and most importantly, they don't change them every year. So getting parts is easy. They are the same as they were 10 or even 20 years ago.

Skid steer are nice at working in tight areas and handling material quickly. If you get one that will handle a bush hog on front, you'll need a machine with the hydraulic capacity to run it. Mulching attachments are expensive and require lots of hydraulic capacity.If you have to mow roads and 7 acres of field with one it will beat you to death. The work you have to do that is suited to a skid steer will be over quickly and a tractor with a front end loader will be useful for maintaining your roads, spraying, and tilling ground. And no, a skid steer isn't the greatest thing to clear land with.

When you go to buy a tractor, I would suggest looking around for an older machine that does not have a computer or need DEF. And that is 4WD. There are tractors out there that come from places so cold they can't use them much in the winter, so they are relatively low houred.

And finally, if you think a 40hp tractor will sufficient, buy a 60. If you want a large bush hot, start looking at 100hp.
 
When had a small 40 acre plot I had both. I used the tractor the most, so owning a tractor and renting a skid steer might be a reasonable option for you if available locally.
 

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