What a drag (it is getting older......)
Now on to the less mundane items:
I surmise that the clutch drags somewhat making the second to first downshift a little balky. Remember, it's a wet clutch so it has oil between the drive and driven plates and that oil actually causes the plates to drag a little. I can't equate that to Hondaxes JD. He's right though, JD's range shift is really balky. I used to look like a fool on my buddy's 4050 searching for a gear. In support of the JD, my Kubota has a hydraulic shuttle with a multi-plate wet clutch and it too, drags a little, making shifting of the main transmission a slow, deliberate shift even though the main box is synchronized.
The R3 clutch would drag more when new and less as it accumulates miles as the plate clearance loosens up somewhat. My '06 Classic is a little balky on the 2-1 downshift and I tend to double clutch it anyway. Double clutching effectively matches the transmission gear speed.