After having just done this I have some experience. Everyone has pretty well described more or less what you can do depending on the preferences of the older man. The operational wt. of a non-weighted JD model G is about 5300 pounds unballasted.
I am not familiar with your winch's rating. Some are rated for pulling up a grade. I had to pull a 3 cylinder Ford 4000 with its front end loader minus bucket up a 30-35 degree grade. All I had was a 5,000 pound Horrible Freight winch. I used a 10,000 pound rated snatch block (Tractor Supply) to double the pull and a secondary 4 ton manual come-along as a safety. This tractor had one low leaky rear and one similar front. Steering it was problematic and nearly impossible since the motor was locked up and the power steering thus inoperable. You know the suggestion of paying a tow truck is good, and I would have used it if I had that as an option.
Your tractor could be used as a stationery anchor for the winch. It would be less likely to slip tires this way. If necessary put chock blocks behind your tractors tires to minimize stress on the gears/brake. Once it is broken free maybe as suggested by previous posts it should roll easily compared to the nightmare I was posed with.
You might not even need a snatch block once it is broken free depending on the ground conditions. If the older man would let you use some of the trees as progressive stationery attachment points (using a tree saver strap/s) this would be best. You might not even need to use your tractor if this is an option. If two men can grunt push a tractor like you want a few feet on level ground, a 4,000 pound winch should do except getting it up a trailer ramp.
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