I like the idea that a Daytona or Sub is cliché, but somehow other models are not. It's Rolex, it is one of the most recognized brand names in the world, and far and away the most recognized luxury watch. Yes, there are a boatload of Subs out there (I think you'll find that Daytonas are tremendously less common, they're a watch nerd favorite, but you couldn't give one away twenty years ago, and there are still stores out there today that pretend to have waiting lists and don't put their steels in the case, not to mention a lot of people don't like crossing into the fifth digit for an all steel watch, and your average Rolex customer -hard as it is for us to believe- doesn't know what the word "comnplication" means), but cliché and iconic are different things. If I wanted a watch I was confident no one else had, I'd steer clear of Rolex. I just find that wearing a watch because it's what others have and not wearing a watch because it's what others have are two sides of the same coin. Wear what you like.
Not trying to criticize your reasons, I actually think you have a fantastic list there that would make for a very nice and fairly rounded collection, just giving my two cents.
My Rolex "collection" is currently just my Milgauss and Hulk. These will not be my last Rolexes by any means, Lord willing. I try not to plan my collection too much honestly, but if I had to say one watch that I really have my sights set on right now, it would be either a platinum Daytona or white gold Sub / GMT. I'm a sucker for the weight, and feel like any of these would have good value retention; just hard to pull the trigger on something at that price. I'd also like to have a nice dressier strap watch at some point, possibly a Prince, but this is one of the few areas it's hard for me not to stray from my Rolex fetish and start looking at some of the other excellent options out there.