The one and only: 16610, 16600, or Omega Speedmaster?

[RTea]

Hi everyone!

First thread posted in this forum but I've been lurking around here for a while soaking in the sights and sounds. I've been around other forums for a while and during my 2-3 years of really getting into watches, I've gone through about 65 watches and haven't found "the one". I'm hoping to finally step it up and get the one watch I've always really wanted so I can end my flipping madness.

I currently own a Pam 25 but find it a little large for comfortable daily wear to the office and on the weekends. That being said, I can't stop drooling over the Sub 16610, Sea Dweller 16600, and Omega Speedmaster Professional Moonphase. The price difference between these 3 can be pretty significant so I was hoping to get some feedback from everyone here before pulling the trigger. Here are my thoughts on each:

Rolex Sub 16610
-Classic sub, goes with anything, can be worn anywhere.
-Wears comfortably but the bracelet and clasp (quality wise) isn't quite on the same level as the Omega.
-Retains its value really well and prices seem to keep climbing
-This is the watch I've always wanted but the Sea Dweller has taken its place since I've gotten into watches
-Cheaper than the Sea Dweller

Rolex Sea Dweller 16600
-Probably my favorite of the subs but prices seemed to have skyrocketed so it seems like I should buy it sooner than later if I'm eventually going to get one
-Love how its a slightly beefed up Sub
-Still fits under cuffs and can be worn in almost any situation
-No cyclops hooray!
-My budget is under $5K so I'd probably have to find one that isn't in tip top shape
-Might be tough to swallow the cost on this but this is more or less the one watch I will want to have in my collection at some time in my life
-Discontinued so not sure where the market will go with these as they are rarer than the 16610

Omega Speedmaster Moonphase 3576.50
-Handwind lemania chronograph movement is a joy to wind and beautiful to look at
-Lovely domed sapphire crystal and sapphire case-back
-Classic moon watch look and vibe with the necessary (for me) added date complication
-Beautifully finished bracelet and clasp
-Limited water resistance, won't feel comfortable wearing this everywhere and submerging it in water
-Can be bought new for the price of a used Sub or can be bought used at significant savings.
-Also a watch I want in my collection sometime

Sorry for all of the text but this is a huge purchase for me and something that's been tearing me apart for quite some time. I love the Speedy and love the Subs but they are very different watches. I'm thinking it would be better to get a Sub now as prices seem to be on the rise and the Speedy is still in production unlike the Sub and Sea Dweller. But I do like the thought of saving quite a bit for a watch as nice as the Speedy and I'm thinking that it might cure my itch for another watch and become my daily wearer.

Any pictures/thoughts/input? I think you can guess which brand I slightly prefer as I posted this in this forum :).