Pete ,
I have been offered a super sweet deal on a John Deere 4440 in great condition. But as part of the deal I would have to part with my open cab 4020. Parting with my beloved 4020 is difficult but it will go to an excellent home and it will get me out of the sun in a newer tractor. My one concern is this will be my only tractor for my small farm. I have about 60 acres of hay to cut , ted , rake and square bale as well as a little custom work. Mowing around the farm and pasture, sprayer, loader work , garden prep and horse arena maintenance. So a lot of utility/small tractor work. A wise old friend once told me “you can do little tractor work with a big tractor but you can’t do big tractor work with a little tractor”. With this being said my main little tractor job that would be a challenge for the 4440 would be raking and grading the horse arena without too much compaction. Any thoughts y’all can share would be awesome.
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I think your friend is indeed very wise. Sage advice. I think you’ll find the 4440 will get 'er done for you. And fact that you got “sweet deal” on it…Congrats!! 4440’s in good to great condition poised to continue hold their value well in the years ahead my gut tells me…and our data tells me this as well 
Hope this was helpful!