I wind mine in the morning when I am wearing the speedy. I look forward to it to be honest, manual wind watches are such a blast.
Jimi, lots of watches will gain or lose depending on the resting position, it is called self regulation. Rolex watches actually tell you in the booklets to try crown up or down depending on if it is fast or slow.
The old saying goes, "crown up, speed it up, crown down, slow it down". Different watches have different little personalities so it will vary. I always try different positions to try to self regulate and figure out how my little mechanical friend likes to sleep. I try dial up, dial down, crown up, crown down. You can even try crown left, crown right, they all make a difference just like in a COSC test.
It all depends if you want to spped up your watch or slow it down.