Only thought that I'd add is that the new oil could be having either a perfectly normal effect or exposing another issue that is tolerable but will ultimately require a repair.
One is that the new lube will obviously be slicker that the old, so you won't have as much friction on the input gear shaft to offset any friction generated by a dirty/sticky/or even completely clean pilot bearing/bushing. If the bearing/bushing is at all sticky, it will continue turning the driveshaft, even with the clutch pedal depressed.
The solution for that is to hold down the clutch pedal for a longer span of time before shifting, to give time for the input shaft to stop spinning. The input still spinning while the back-end gears are sitting still is what leads to what I call the classic Farmall crunch or grind when engaging in a gear.
The other side is that 3rd (not so fast) and fourth (really fast as these things go) gears spin faster than 1st and 2nd, so it takes a little more finesse to engage them. It has to do with the relative speeds of the powered vs. the driven gears are spinning. The difference in 3rd is noticably more that 1st or 2nd, but doesn't begin to compare with 4th (your "road" gear).
If you're not having a crunch or grind, it could bery well be what mkirsch suggested, in which case you'll wanna pull the cover/shifter off and clean things up and look for wear, especially on the 3rd gear side. Or for any crud that might be binding up the shifter on those gears.
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Today's Featured Article - Timing Your Magneto Ignition Tractor - by Chris Pratt. If you have done major engine work or restored your tractor, chances are you removed the magneto and spark plug wires and eventually reached the point where you had to put it all back together and make it run. On our first cosmetic restoration, not having a manual, we carefully marked the wires, taped the magneto in the position it came off, and were careful not to turn the engine over while we had these components off. We thought we could get by with this since the engine ran perfectly and would not need any internal work. After the cleanup and painting was done, we began reassembly and finally came to t
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