I'm a sucker for the date window too...but I dunno..the medium one didn't really WOW me in anyway..kind of like...yeah, it's there..I guess..understated elegance..in the long run the medium probably would be better? Having a hard time convincing myself.. I'll have to go back and try again.....and again..I don't think I'll be spending this kind of money on another watch for a long time..
If it didn't wow you, you absolutely shouldn't get it. Sounds to me like you love the Large, but def go try again.
Here is another enabling pic.