1 getting the trees out and getting cash
2 stump removal
3 little surface roots (just under the surface)
4 leveling things out (clean up of all of above)
5 planting / dealing with orchard and general maintenance
1and 2 are bigger jobs, 3 and 4 can be big jobs as well. 5 is were your tractor is going to come in at.
2 through 5 you might get away with a small amount of acreage. but you are talking a lot of acres. and you would be wasting more time / money on a small tractor vs bigger machinery. since you won't need the bigger machinery afterwards. you are stuck at...
A. paying someone else to do it
B. renting and doing it yourself
C. buying a used machine/s and doing it yourself. then selling after you get done.
a Professional operator can do a lot quicker and faster. while driving machinery around, and operating the hydraulics are easy enough on most machines and a few hours in the seat i would imagine most folks get hang of it, it is the extra experience, of moving stuff around, and working around the rain. working the dirt, etc... and more so an operator that knows the machine (used it multi times) and knows the power of the machine / traction of the machine, how much they can bite into stuff without getting stuck.
(B) option aka renting and do it yourself. there is still some maintenance involved. greasing, checking fluids, checking tracks if machine has tracks. making sure you have enough fuel on hand to keep the machinery going.
i have went route of (C) i am no professional by no means. and have made some pretty big messes. but have learned, and has allowed me to drag stuff out longer. but you need to have some "mechanical skills" repairing stuff. shop/service manual for the machinery, and some searching on youtube / google brings back enough so far, for me to fix general things that have went wrong. but it takes time. and the correct tools.
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goal of above more along the lines, of trying to give ya basic options folks end up looking through...
regardless of what you do above. i tend to goto google type in my address, click on "maps" (76 or something acres here), and then click on "earth" one of the icons along the bottom of the map. zoom in all the way. and print a few maps out.
there are a couple other sites such as "terraserver.com" that give "elevation" maps as well.
with above i'am able to use markers and like and figure out locations for a road way, lake, garden etc... fairly easily. and when i show them to someone else. they get idea quickly. without much effort.
below images.. i did....
print screen key (PRTSCN) top right hand corner of your keyboard.
opened up (paint) comes with all versions of microsoft windows computers
pressed (CTRL + V) keys for paste. used the rectangular selection tool and pressed crop. used the line tool to put in fence line / boarder lines.
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above is more an attempt to get a "plan" and get it down on paper. so when working with 3rd party companies / folks coming in. you have an easy way of saying hey this here, that there. driveway there, road/gravel roadway there, fence line there, a row of trees here. tree root balls here, get dirt from over here, etc...