you made some very strong points! First, having to get up there in pitching seas is no fun, especially with no place to brace. I was somewhat worried about that with my plan to use an anchor winch. That is one of the reasons that I was looking at that solution, I am well over the 200 mark and I am not fat... Railing seemed to give some sense of security, but like I said, I am well over the 200# mark and the momentum of my body against the railing wouldn't be pretty. So I am thinking possibly I need to rethink my plans. I had considered the hatch in the cuddy as you mentioned, and I think that I will probably do that regardless. It would be nice to be able to access the bow without hanging my big butt over the side in rough conditions.
Some notes on anchor windlasses: there is a vertical post model and a horizontal post model. The horizontal post model works better and deposits the rode (chain or rope) in the anchor well. The vertical post requires more fall, 18" or more in order to work best. The horizontal model deposits the rode through a hatch or hole into the locker. I was not thinking of the spool variety, I have never been a fan of that type of winch. An example of the windlass I was considering https://www.fisheriessupply.com/lewmar-pro-fish-horizontal-windlass
I have also considered the Columbia river system which I have used for years. It works off of a pulley system and a buoy much like you mentioned. A lot less work than hauling an anchor rode of 300 plus feet along with an anchor on the end. this system works very well, but the more chain, the more you have to do by hand. http://cdn.shopify.com/s/files/1/0266/2799/products/buoy_ball-and-anchor_puller-complete_400_1024x1024.jpg?v=1378666903
Anchoring on the Columbia can be a life or death situation, determined by how safe you make it and your proximity to others or their proximity to you. It gets real hairy when some idiot doesn't know what he is doing and hooks up to your rode...
In any event, the latter system was my original choice, but I was looking to spend less time on the bow. The windlass can be operated with a simple switch, and handles both rope and chain. That means that 1.) I'm not on the bow 99% of the time and B.) I can go with my own choice in rode length which is not possible with the fixed spool model.
Bullet: As far as the anchor well draining, it would drain just like the original does, through scuppers at the back corners on either side.