The 399 would be 10 years or so newer than the 1085 and about 10-15 HP more. The 285 is the utility version of the same tractor and that's what we have.
Great tractor and pretty economical. 318 4 cyl Perkins that puts out 85 HP. 540 PTO, and if you can find a 1000 RPM shaft they have 1000 RPM capabilties as well. I'm guessing your rake would be a hydraulic driven model? Should work.
Drove a 399 once or twice on a relatives farm, but can't tell you much about them. Was a good tractor though. Don't know much about the rest of the models you listed either.
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