I wouldn't worry about winding every day. It takes less than a minute and quickly becomes just another bit of routine. I actually prefer handwound watches to autos, but that's quite rare.
Personally I'm not a believer in taking any high-end watch diving. If I am diving, an expensive watch is just another distraction. There are plenty of watches that can go deep for cheap, and I really see no reason to drag a real nice one down to that environment. The fish certainly don't care.
If you get a Poljot you should definately get the glass back. Thats a great way to appreciate the mechanism in the watch, and explain it to the Timex and G-Shock crowd. While conceivably it could represent a failure point, I can't imagine what ordinary activity would cause this to happen. Mine has held up just fine.
If you really have to have a nice watch that is also good for diving I would recommend one of the Seiko 7S26 auto divers. Not nearly as nice or refined as a Poljot or as advanced as the Citizen, but a good enough watch and perfectly at home in deep water.