Wow! Great to have someone from 4K+ miles away to participate. Thanks PTSG!
Regarding having any gears grinding or other odd transmission behavior, the answer is no. I always used the clutch and never forced the tractor into gear.
As I mentioned above, I grew up on farm. I learned to drive on a Ford 8N and drove an Oliver 77 for many years bailing hay. Additionally, I had time on three Massey Fergusons - 235, 265, and Super 90. After I left home my Dad added a 2-85 White. I'd drive it on occasion for spring tilling. No issues with the transmissions driving any of those tractors.
I don't know if it's a contributing factor. Along with tilling, planting, and rotary cutting, I used my CK3510 to plow snow off my driveway. Some years it snows more than others, causing more winter hours. One winter, my wife and I cleaned up over a two dozen large willows and box elders that came down in a wind storm. That probably put 30+ hours of 0-20 degree F on the tractor. I skidded the trees and piled them with the loader into a large brush pile.
I mentioned the winter usage as that's when the transmission acted up, both times, while plowing snow. I attempting to shift from 2nd into R, when the transmission didn't want to come out of 2nd gear. Really startled me as I had never experience a tractor getting stuck in a gear. Sticking in 2nd and R became progressively worse. That led to the dealer replacing the synchronizer hubs and rings.
Similar, I was plowing snow when I shifted the tractor into 1st gear to scrape hard pack snow off of a concrete apron. I was in L or M range. When I left the clutch out the gears ground. Never have experienced that happening in the past either. It took me a while to discover, if I kept the range in neutral, shifted into 1st and released the clutch, and then depressed the clutch and selected the range, the transmission would work.
I'm glad to hear you've had no transmission issues with your tractors, that's fantastic! Hopefully I'll get mine figured out.