The problem with a question like this on an internet Forum, especially one so strongly focused on the visual (watch images) like OmegaForums, is that it has no mechanism for effectively conveying aspects relating to our other important senses, namely touch and sound.
How to put into words such aspects? Perhaps using the most relevant onomatopoeic word: Haptics (pronounced Hap-Ticks).
There are endless images of beautiful vintage and modern Speedmasters here on OF, but not one single one of them prepared me for the simple, delightful revelation of having to wind up the Speedmaster’s mechanical watch movement.
While it is of course possible and often necessary to wind up some of my automatics if they haven’t been used for a while, the winding action and sensory feedback is quite different on the automatics to my caliber 861 Speedmaster with steel case and Hesalite crystal and different again comparing it with a new, unused Speedmaster with an 1861 movement and Sapphire crystal. They all transmit the sound and mechanical pulses differently to your senses.
The way my Speedie makes those strong (clockwise) and gentle (anti clockwise) clicks if you roll the crown back and forth between your thumb and forefinger or that “seeee-thrup” sort of sound if you just wind clockwise and release the crown is unique and strangely rewarding in and of itself.
So, no, not a pain at all. Quite the contrary in fact. It is a must have experience for any watch enthusiast.