I agree with James. The Deere will be the easiest to maintain, but also get a feel for you local dealer. Both our CaseIH dealer and the Deere dealer we deal with are great. Go out of there way even for our very small operation.
The IH 1066 and 1086 were very good strong tractors. The torque amplifiers were kind of a weak spot but for 50 acrers pobably won't be an issue. I never liked the stacked PTO's due to the 540 shaft never seemed to line up right. These were also cold blooded compared to a Deere 20 or 40 series. Parts aren't always stocked, but usually a day away.
The 30 series are reliable tractors, just don't start good or have the torque rise of other Deere models.
Search these forum and you will find lots more information.
I have worked in central NY with winter temps down to twenty plus below 0, Many a green farmer with 20 through 40 series that owned a red tractor for the manure spreader because as they would say "they start better unplugged then the green ones plugged in!
Watch the 30 series, they had the same rear end as he 20 series and with the added weight they did have an update to the 40 series as they had a lot of failures within the first few years.
I hadn't heard any farmer who disliked the two pto's on the back of the red tractors, beat having the oil running out because of not backing up step enough of a slope to have the oil running out the back when changing shafts from 1000 to 540 or vise-versa.
The torque amplifiers when used properly would last 7,000-8,000 hours and longer. When used as a brake for the tractor to slow down they normally ran about 2,500 hours before failure. Many failures happened because of lack of knowledge of proper adjustments as well as the charge pump to the system got weak and kept driving and using the tractor because it still worked some!
I don't know where other then you are more familier with the deere line that they are easier to work on? Pto job on red, four hours, deere split it! Brake job on red four hours, deere split it!
Watch out for those that just had new pumps put in but not a brake job! Older deere's only filters the return not the pick-up on the oil so the first sign of the brake failure is actually the hydraulic pump failure!