skim read through your thread.
trees and stumps, washouts, trenches for field tile to septic line, retaining wall, snow removal, assuming rock drive way, 20 to 30 percent slope.
the small things....
general duty bucket for front loader, be nice to have a good clean cutting edge, and possibly removeable teeth for the bucket, 2 to 3 hooks on top of bucket and most likely top of bucket re-enforced for the hooks. (hooks make it nice for chains)
it would be nice to have a grabber attachment for general duty front end laoder bucket, or a 4 in 1 bucket, for front loader. but that would be extra and would say you could live without the grabber or 4 in 1 bucket. but you know your projects and land better than anyone. and it could easily swap type of bucket you go with.
3pt hitch backhoe with subframe. would be very good thing, granted it may take time for larger stumps but could be douable. if it was only stump here or there through out the years ok. but if you are wanting a large amount of stumps done, gas for tractor, plus hassle and headaches, i would hire it out or rent a mini excavator or have a dozer come in. on other hand personally can not live without a backhoe they come in real handy many times, and from sounds of it a backhoe would make life easier and would pay for itself fairly easily.
i would at min go with a mechanical "thumb" for the backhoe. it can make life easier more so with some of the projects i read you might have.
most likely you will end up with a 3pt hitch rear blade, and a box blade. partly for snow, party to deal with gravel drive way, partly to re-work your landscape and get things smooth again.
a bush hog many folks call them but rottory cutter, for dealing with tall weeds and brush. you could pick up a used smaller size unit, to help deal weeds and like. and then use a finishing mower (belly mower or 3pt hitch) to cut grass regularly.
you will most likely want some sort of tool box on tractor. and another spot to place some chains,
possible a 3pt hitch carry all. to deal with say fire wood, or moving tools from one place to another place. it is either a carry-all or 3pt forks. or perhaps forks that fit on the front bucket of tractor.
pending on driveway and how it slopes, possibly chains for rear tires.
myself, i require rear tire "diffential lock" so i can lock both tires so they spin the exact same speed. gets me out of alot of stuck situations, and keeps me moving. i also require left and right rear break pedals, they come in very handy, both getting unstuck, but also stearing around some things. personally prefer gas pedal one foot, left and right back rear brake pedals other foot. MFWD or rather 4x4 drive is always nice, but differential lock and left and right rear break pedals, are extremely nice.
you have enough projects, and in that seat time, i would hate manual shifting and constantly pushing the foot clutch in. i would suggest finding something that avoids this as much as possible for the tranmission. there is way to much forward reversing, changing gears, it is like manual tranmission in a truck, and having to go from a dead stop to 1st, 2nd, 3rd gear. every 2 minutes the entire day. it is a killer pushing a foot clutch in all the time.
min 1 rear remote, do you really need a snow blower? a rear blade and front end loader general duty bucket can do the job pretty good, though if you have rear left and right break pedals it can make for easier spinning around on ice / snow to dump snow off to the side. though if driveway is narrow and steep on one or both sides, snow blower may be a big ticket requirement. and would say put money into a wind block around the seat first. keeping wind off you can be a bigger ticket in winter, at least for me.
postiton control. or rather, raise and lower a 3pt hitch implement and it stays were you want it. is extremely nice and needed for a few things.
it is not needed, but if you had spare cash, i would say place it into a TNT (top and tilt) for the 3pt hitch, and the extra joystick or levelers and hyd remotes for it. and if you think you will go for TNT later on when cash is avilable, i would say, get the extra remotes now when buying the tractor. due to it will more likely be cheaper now buying everything together. vs down road. and possibly hauling trackter into a dealer and paying dealer hourly costs. vs possibly reduced labor costs when buying all at same time.
for me, there is never enough day light, more so this time of year. having a min of one rear work light is a blessing. it is a pain, not being able to see things while hooking up or unhooking things, when it goes dark. while head lights are on all tractors, having 2 work lights mounted to say the ROPS (roll over protection) facing forward can make life easier as well. more so when you have a front end loader. head lights end up getting blocked by the bucket, and you can not see were the bucket is in location to the ground and at what angle. and those front work lights can make those 30 minutes to 1 hour after sun sets more productive vs placing the tractor into the shed.
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to the above, you have enough lawn, and enough projects. that yes if money is tight getting one tractor is good. but enough lawn and hassles, i would say get 2 tractors one just for mowing, and then a second tractor for everything else. mowing = to much seat time. all the other projects = multi purpose doings, and you might be better served with a bigger tractor to reduce seat time and getting things done. granted to me a scut (sub compact utilty tractor) is an over size lawn mower. and CUT (compact utitly tractor) there can be a change over in overall "frame" were everything sets higher and more ground clearance in getting through mud and snow. 2 tractors mean perhaps going with ag tires vs turf tires. to deal with mud and snow traction better. and then turf tires for the regular lawn mower. to keep grass looking better and not tearing it up when just mowing.
a bigger tractor is always nice, but all the little extras add up very quickly. but it is those extras, that can make or break a deal. and make your life easier. and could but a bigger tractor with extreme basics, vs having a smaller tractor with all the extras. a tough choice. for me, i would say i want the extras. and implements vs just a larger tractor with very basics that limit what i can do. it may mean more seat time for larger projects. but...*shrugs* on other hand, if you are fairly mechanically inclined. and have the basic tools already, it very well may by more worth it to go with a bigger tractor, and secondary lawn mower, and then as time / money / projects need to be done, add things to the tractor as needed. there is a good third party market for many things. but ya need to be mechanically inclined to take advantage of it. without paying out more cash long haul.
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again with others, if you are going to be clearing out a good amount of trees. hire it out, or rent a bigger tractor or dozer for that. and then get something that should fit majority of all your other projects.
i realize renting or hiring it out. including myself. i do not like doing. DIY'er here. but there is a point between taking forever and twiddling your thumbs, vs getting it done and being done with it, and moving on to next project.