I'd go with a Massey 255 before a 165 honestly.. 165's get stuck on a banana peel, they had much lighter rear ends.. In the masseys, wet brakes are also very desirable, the dry brakes are always grabby and wear more.. some models came with either as an option.. Also, I'm not too fond of the 165 diesel engine, while they do last, they don't have much grunt IMHO.. and they're a very shaky engine, the 255 has a far smoother feel to it. Another difference between the two is the 165 has a pretty complicated steering system, all fine and dandy while things are tight, but hard to fix and tighten if it's been abused.. the 255 has full power steering which has no steering box, just a servo.
Both tractors came with the 4 speed or 3 speed with multi-power (half speed).. (both had high and low range) good and bad points to each.. the 4 speed has a big step between 2nd and 3rd like many tractors of that era (WHY @#$#$%#$????), but the 3 speed doesn't engine brake when multipower is in low.. coupled with grabby brakes on a 165 and perhaps an operator that isn't well aware of this, it could turn out bad.. Is your land steep?
I think the 3 speeds had fully independent PTO while the 4 speeds had a 2 stage clutch.. again, good and bad points to each.. the independent one brakes and locks the PTO, so if you can't turn the implement shaft to get the splines to line up, you're going to be swearing a bit... I found them to be a safety concern too, your pant leg will easily engage the PTO by accident and they can be half engaged.. If you have a bound up cutter or something and free it, there will be drag and it could start moving again.. the 2 stage clutch PTO is a physical gear, it'll grind if you try and engage it rather than go in...
