No offence to the OP here but I fail to see how a Rolex or any other dive watch can be compared sensibly to the Apple watch. One is a mechanical wristwatch engineered to tell the time and in some cases the date, time your dive etc. The other is a wrist mounted gadget that is effectively a remote control for your iPhone. They are not even remotely close in who they are designed to target.
If you buy a Rolex it will always be a Rolex. You can pass it on after you die and it will always be worth quite a lot of money. You don't lose a lot on your investment. The current Apple watch is a cool gadget but ultimately in many years to come it will either be completely redundant and sat in the back of a drawer gathering dust, or recycled into something else. Rolex have a rich history in timekeeping and decades of brand prestige. It's perfectly possible to own both (if you can) but in this scenario it's not one or the other. One is a luxury watch and an investment and the other is an electronic wearable that will have a shelf life like anything else in its category.
If I add up how much I've spent on iPhones, I could have bought an Omega Seamaster. Guess which one will still be relevant in 20 years time?
Clearly the two are aimed at entirely different audiences and one is destined to be a keepsake and the other is probably destined to be recycled. When I started this thread I was thinking about choosing a watch for what it does for me today, not my grandkids or my investment advisor's opinion of how well I spend my money. From that viewpoint, the two can be considered competitors as Apple Edition watches sell in some of the same price points as Rolex watches and an Apple watch sport sells at almost exactly the same price point as my now idled Citizen Eco Drive. As I mentioned in the opening post, I looked at diving watches and Rolex watches to see how they felt and to imagine what they could do for me before I got a chance to go to the Apple store for one of their "try on" appointments. I've owned a Rolex (clone) and while it felt nice and looked (mostly) nice (for a while), all it did was tell the time. My Apple watch does quite a bit more. Granted a diving watch (if it has a depth meter) can do something my Apple watch can't but I need to read email and texts and check the weather a whole lot more often than I need a depth meter.
Many in this thread have predicted the demise of Rolex watches if they don't offer something "smart." Partly from reading other responses in this thread I find that I do not agree. Yet. It's too early to tell. Recent articles say Apple watch "might" be selling "below analyst expectations". Apple is not (often) known to pump money into a losing product. Microsoft did so and brought Xbox from irrelevant to arguably the best console. If Apple, which has very deep pockets by the way, decides to stick with Apple watch despite it's (allegedly) lukewarm reception, they will eventually figure out the killer app that has people lining up for them. That would be the time when the Swiss jewelers and the Japanese technologists would be forced to sit up and take notice. Apple has a recent track record of making sure that by the time competitors notices Apple is beginning to dominate, it is already too late. Just as iPod buried Walkman and iPhone buried Blackberry, Palm and PocketPC, it is possible Apple watch will come along and bury a lot of today's watchmakers. Not necessarily because the first Apple watch is so wonderful, but because Apple is so adept at disruption.
I've owned some very nice automatic mechanical and eco drive watches yet I was on Apple's site preordering early one morning in April because I knew that I wanted more out of a watch than what I was getting before Apple watch. If you look around, you see a lot of people still wearing watches despite the fact their smartphone is somewhere on their person in a pocket or purse.
This is the key difference between a phone and a watch, smart or otherwise.
To glance at my wrist merely by tilting it slightly, I can read a text or check the time or weather. Chances are nobody in a meeting will be distracted by someone with a smartwatch digging through their pocket, briefcase or purse for their phone. Will Rolex cave and make a smart(er) watch? I doubt it. I think they are perfectly happy with their tiny niche of the top end watch market unless Apple edition watches are proven to be taking prospective Rolex customers. But Citizen and Seiko had better start paying attention sooner rather than later.
As for adding up how much I've spent on smartphones and other Apple gear, let's just say Apple should name a sizable segment of that new spaceship campus in my honor.

Still other posters in this thread did an excellent job of analyzing the net present value of purchasing Apple watch versus Rolex. Those same calculations could analyze the purchase of the pile of Apple gear I've bought. But you know what? I'll take my Apple gear over a dozen submariners. I didn't have to go in debt to buy it, it works for what I need it to do and to me that's all that matters.