i am one for a backhoe. i can not live without one now.
as far as gravel road. box blade, rear blade, some sort of rake, would be suggested.
box blade, is good at moving materials and leveling the road, and if need be putting a slight slope to the road for run off water.
read blade, can be quick easy way to remove snow off the road, and also helps on gravel roads to help "bring" gravel off on the sides of the road back into the road.
a land plane, is what i am still drooling over and really wanting one. and can revive a old gravel road, by bring rocks up out of the dirt and back on top.
a rake, can help bring rocks back into the road, after "snow removal" and all the snow melts and you have rocks all over the place.
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if you are looking at a bush hog / rotatory cutter. you may want some sort of "front weight" make that a FEL (front end loader), or suit case weights on the front. rotatory cutter, is what most use to cut down tall weeds in a pasture or down fence lines.
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some folks will either save up a bunch of projects, and then rent a excavator (backhoe on tracks). and be done with it. say cut down a bunch of trees and dealing with stumps, wait on digging a trench for a new pipe for say electrical or water or something.
myself prefer a backhoe though, preferably one i can detach and use rear 3pt hitch and pto for other equipment. myself tend to use backhoe, to pull fence posts, dig trenches, stump removal, put in culverts, and compact dirt around the culverts as i back fill. if i am putting in "steel fence posts" i will use the back hoe to just push the suckers right down into the ground. tend to use backhoe to load/unload the trailer, when dealing with heavier stuff vs the FEL. backhoe allows more maneuverability. and the BIG ONE, getting my rear "unstuck" out of muddy mess, that i got myself into.
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if you are looking at digging with (fel) front end loader, 4wd can help, so can a "tooth bar" instead of a generic cutting edge, on the bucket.
if you are cleaning up wooded area, or pasture, a backhoe with thumb on it, or a grabble on the front bucket of the FEL. can help go up and grab a bush or like and rip it out, and then drive to some common area, to dump it, for burning or burring.
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as far as tractor itself. more so in a tractor that will be a jack of all trades, and doing a variety of tasks with. prefer "left and right steering brakes" for the back wheels. allows for tighter turns, and at times help me get unstuck. tigher turns, comes into play getting in some ugly situations in the woods. were there just not enough room to really steer around a tree or something on the ground.
differential lock, for rear wheels, can help a good amount, to get yourself unstuck. most tractors regardless of 2wd or 4wd. will only put power out to one or 2 tires (2wd drive to only 1 rear tire), (4wd, only to 1 rear tire and only to 1 front tire) , differential lock, makes it so both rear tires get power. been times on snow/ice removal to getting out of a muddy mess this has helped me. on a 2wd tractor.
I HATE FOOT CLUTCHES, just like a manual stick truck or car. every time you change gears or need to go forward or reverse you have to push the clutch in. there been to many times, i felt like my foot and entire leg was cut off at the hip. from pushing in the clutch so many times. a tractor that either allows a quick push button on the gear shifter helps alot! to just change gears or to go forward or reverse.
have rear work light or 2, if you are a DIY'er, you can normally fairly easily add these later on, they might be a bell or whistle. but boy, to many nights i wished i had them. from plowing snow from getting home to work, and no sun light to speak of. to spring / fall and getting out there to do something only to have dark hit you. and wanting to do last minute work.
2 sets of hydraulic hooks in the rear. should handle majority of any sort of attachments you might get.
the exception to the above, is TNT (top N tilt) for the 3pt hitch. most 3pt hitches have some sort of turn buckle. "large bolt" with a nut you can turn, to adjust the arms of the 3pt hitch. and then another turn buckle for the very top 3pt hitch connection. TNT = hydraulic cylinders vs turn buckles. can make life easier, if you have a good amount of curvy roads to deal with, were every 50 feet or so requires a different slope in the road. you can quickly adjust angle of box blade or rear blade is set to. without ever getting off the tractor, by just using a couple levers. ((this would be a bells and whistles)) TNT = requires extra hydraulic hookups pending on 3PT implement you use.
TIRES, as long as you are not using tractor as a mowing tractor for your front yard. i would say "ag" style tires. they provide good grip in mud, and less likely to get stuck. but they can tear up a front yard up pretty quick.
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is it worth going for all the bells and whistles, or getting a bigger tractor with just the basics?
smaller tractor with say enclosed cab, rear and front work lights, heated cab, extra hydraulic hooks on rear, TNT (top n tilt), 4wd, loader. with a heavy duty bucket.
vs a larger tractor with (open station = NO CAB) with a couple hydraulic hooks in back and a loader. more power is always nice. and gives you more pulling power, to say drag a tree up out the woods into a better area to cut and split the wood, take bigger chunks out of road, for say plowing snow, or grading the gravel road. vs taking extra passes down the road, and needing to go back and forth a few times to move larger snow drifts.
smaller tractor with everything, yes does take more time to do things, but the extra bells and whistles, can give a better end result. not needing to be bundled in a few layers of cloths during winter as you plow the snow. able to manovuer in the pasture and around trees and like easier due to smaller size. able to quickly adjust box blade and/or rear blade quickly with TNT vs getting off tractor to make adjustments (good for curved / hilly roads) con is, everything just takes longer, for grunt work, on a smaller tractor.
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everything above said, look at all major brands out there. and physically set down on some of them. some of them have some pretty funny setups, of were levers and peddles are. for some folks the setup is perfect. for what they will be using tractor for, and the uses of the tractor that require this or that, the funny setup is ok.
myself, is brake pedals, and gas pedal being on different sides. or are large enough i can place both feet into the area. so i can hold down left or right back brake pedal, while adjusting gas pedal to get myself unstuck.
other is gear shifter, and then 2 levers or joystick for FEL (front end loader) and having them in a easy access area, that does not require me to "stretch" or turn my arm some how to use.
3pt hitch raising / lowering, and then turning on/off the PTO in the rear is a big one for me. i do not like reaching between my legs to pull (something out of my rear) eerr move a lever. other adjustments ok. but not raising and lower and turning on/off pto.
tractors do not have any sort of suspension like cars and trucks do. so any sort of "bump" you go over. you feel in your rear. you may not notice anything just test driving tractor around at a dealer ship. but if you filled the FEL (front end loader) up with a full bucket of dirt. and got up into a higher gear to move faster and purposely hit a few bumps, that seat suspension can be quickly found out. be careful! have hit a few bumps that sent me flying up out of the seat before.
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other misc things that normally i do not see come on a tractor...
FEL hooks, for chains or like. that are mounted across the top edge of the bucket. used multi times for trees, to using FEL to move stuff around the farm.
places to hang a 5 gallon buckets from, for carry chains, to tools. or tool box large enough to carry a hammer, some channel locks, some wire, some pins, and like in. for when things break. you have enough to temp fix, to get yourself back to the shed.