I'm posting my reply without having read anyone else's. I figure I will go back later and see where we have common thoughts.
I've currently got both. The 1086 is actually gone but I use my 886 everyday for chores. They don't have many differences. Here's what I notice:
The 86 series has a far superior cab feel. It feels much larger and only has the "tailpipe" to obstruct view. The rear window hinges far out. I like where the radio and HVAC controls are much better. I think the three point is more responsive to small movements and easier to feather as well as the PTO the same. I really like how a door is operational on either side. I don't use the right hand door because I have a joystick loader stand in the way but it is nice to open that door and operate the hydraulics or loader from the ground. I'm hugely annoyed by the forward hinged doors and just about trip myself getting out about once a day. I think the cab is noisier. The seat does not offer much movement for someone who is 6'4" but the cab is wider so I can sit sideways a bit. I hate the vinyl seat - it makes for a sweaty rearend. I think the IH cab stays much cleaner and less dusty than the Soundguard cab. I like that I can see the hitch without smacking my head on the rear glass. Although I wish it had powershift/quad shift, I shift through the gears on my 886 like a semi truck and never grind the gears. I find that I shift less because the TA is just the right jump down when moving bales, etc. Why in the world they couldn't put a tilting wheel in that tractor is beyond me. There's no way to get that steering wheel out of my way - it's like the old 4020!
The door on the 4440 is far more user friendly. It gets out of your way and isn't blown shut by the slightest breeze when you are half way in. The throttle lever and remotes are in an excellent place for the user. I think the gauge package is far more reliable/accurate. I trust them more. I really dislike looking around that exhaust and the door frame. I also am driven nuts by the 8 inches of space between the clutch pedal and the wheel well. I think it is harder to keep a Soundguard cab looking nice because you are so close to cloth areas your pliers are rubbing on them, etc. My 4440 is ready for its third cab kit. I like that I can start the tractor from the ground and have it limbering up while I load the cab for my day. I do hate the manual shutoff setup, though. The plastic around the cable pull can be broken pretty easily when you leave your tractor at Deere for repairs. Don't ask how I know. There sure isn't much floor space for my big cup and other things in a JD cab. The quad shift goes without saying. I dearly love it.
I wouldn't be able to do without either tractor. I love them both. I grew up only IH but have always farmed with Deere as an adult because of the support network. I made the conscious decision to find an 86 series despite a few of its shortcomings. It really isn't a big jump from one to the other each day. Both companies made a good product. All of my machines have held up well and I am proud to have people see what I am pulling my equipment with. A local auctioneer mentioned yesterday that he knew I only bought "nice things" and that I am picky about my equipment. I don't care how old it is, it should function the way it did when it left the factory in every respect. Both the 886 and 4440 fit that bill. Good solid dependable tractors that perform well if maintained.
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Today's Featured Article - Product Review: Black Tire Paint - by Staff. I have been fortunate in that two of my tractors have had rear tires that were in great shape when I bought the tractor. My model "H" even had the old style fronts with plenty of tread. My "L" fronts were mismatched Sears Guardsman snow tires, which I promptly tossed. Well, although these tires were in good shape as far as tread was concerned, they looked real sad. All were flat, but new tubes fixed that. In addition to years and years of scuffing and fading, they had paint splattered on
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