That is one of those judgement calls, that can be difficult to make an accurate assessment, what kind of tractor is the jd 2040, is it similar to the other row crops, anything like a 2010 or is it more like a utility type? (can't visualize what kind that model is) I know the feeling well having been on a 2010 narrow front in a few places I'd like to forget about, that feeling is unique. First thing is, no hill is worth mowing that will potentially turn over a tractor with you on it, even more so if it does not have a roll over protective structure and seat with seatbelt, designed and manufactured to keep you in place and not fail under load (crush, bend, break etc.) you stay in the seat and are not crushed by the tractor. Without that, it's russian roulette, goes over you lose. Another thing I hate about hills, is the potential to free wheel, anyting prone to pop out of gear etc., can also be a factor, nice to have good brakes. Always remember fresh cut grass, weeds whatever is slippery, and that dew when the sun goes down is also just as slippery. Best thing for hills is a low center of gravity utility sized tractor properly ballasted and or weighted down, or any similar piece of equipment designed for the purpose, vs a row crop or other higher center of gravity type of tractor. Also not to lecture, but these hills can really get under your skin so to speak and test your nerve, I often look at areas I'd like to mow and just talk myself out of it, + all the unknowns, that new chuck hole on the down side wheels, who knows what, if it's unfamiliar turf, heavily over grown, anything is possible. We have an abundance of hills here, actually not too far from the MA border about 25 miles, (I can see the berkshires from my house) and it's amazed me that in some of the fields I've been in, particularly a few from last year I noticed that some of the slopes certainly were not friendly to the larger higher center of gravity tractors commonly used. I loaded out hay, large sqaures and rounds out of those fields, and knowing that the big ford NH 8970 made it through there, still did not have me convinced, I skidded many bales to safer ground before picking and loading. 
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