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If it is any consolation or cause for hope, I have a first year 4300 that experienced more than its share of problems - but not quite as many as your 4400. The dealer picked up the tractor, fixed the problem each time and then delivered it back to me. When my transmission went, he gave me two loaners - a 4400 and a 955(?).
Since then my warrenty has expired, but I have had no further problems. I am now at about 250 hours.
If I were you I would press for a replacement or extended warrenty. If all else fails, perhaps things will get better after the problems are all taken care of.

4400 lemon
John Deere Tractors
Replies 9 Post by Wi_Doug

I have a similar problem with my 4300 HST. I think that part of it is hitting the back of the shroud that is around the range shifter. I have noticed that the latest models have more clearance or a shorter throw as they engage the C range before reaching the back of the channel. I do not think there is much in the way of adjustment that I can see as the handle goes directly into the rear end. If there is an adjustment, please let me know.

C range on 4400 rear end
John Deere Tractors
Replies 5 Post by wi_Doug

I have a 4300 and a 72"mmm. It works just fine. In heavy grass it can bog down a bit. I either take a smaller cut [cut only 2/3 the width of the deck] or raise the deck a bit and then take a second pass. Wet grass will slow it down more than deep grass.
Going up hill with the mower going through heavy grass, the tractor slows. I ease up on the hydro and go the rest of the way up the hill OK.
It does not cut as well as a bush hog in really deep grass [like 6' tall big blue stem], thistle or burdock. They tend to bend over and the blades are past before it pops up again.

4300 and 72 mmm - power
John Deere Tractors
Replies 3 Post by wi_Doug