I actually had the opposite experience. When I first went and tried on the Speedmaster at an AD I felt a little underwhelmed. It looked a bit small, felt a bit light, and didn't look all that great under the bright artificial lights of the store. Luckily after a few more months I bought one anyway, and the actual wearing experience has been nothing short of amazing. It looks SO good in natural light and other various lighting conditions. The size is great now that I have the bracelet sized right and it's wearing naturally on the wrist. And the weight is great...makes a very comfortable watch for me.
As for the hand winding, I'll admit it's not the easiest to access the crown. For me, it's more the overhanging bezel that's the issue...not the crown guards. But the crown is so smooth and easy to turn it's not been an issue at all, and I love giving the watch "life" each morning when I wind it up.