I like the traditional Speedmaster. I don't like those limited edition ones (like the Apollo 40th anniversary one)
I have never had problem with winding the watch up manually. I actually wind it up every 2 days (Mon,Wed, Fri) on weeks that I wear it.
I wind it in the morning before I put it on. Takes a big 2-6 seconds to wind it.
The watches I find super annoying to manually wind each day are the couple of Vostoks and my Rolex 6694 because you have to unscrew the crown and then wind it and then screw the crown back down which is annoying to me because I always fear cross threading the crown.
That said, I do wish the Speedmaster was at least 100m water resistance