You are looking at a rather high-end of the spectrum. I honestly don't see a logical comparison between the Carrera 02, and any of the Rolexes available, at least not in terms of design, look and feel, and overall lifestyle.
You'll have to ask yourself a couple of questions before taking the plunge; are you looking for a classic sedan, or a sportier coupe?
If you truly liked the 02 so much, obviously for it being avant-garde and contemporary - why look to the most rational alternative that is Rolex?
15K can get you a lot of things.
I cannot deny the Daytona is a beautiful watch; it is classy, elegant. The TH, is more modern, more audacious.
The IWC Portuguese on the other hand, doesn't fit in here. It is much more refined than both.
Is it thus for the value for money / resale value only? Keeping in mind a "daily" over he span of a couple of years will be challenging to keep in mint condition.
Rolex do depreciate as well, maybe not as much as a TH, true.
Finally, do you worry TH might not be perceived as well in social milieus? Not as fancy as a Rolex, Panerai, or IWC?
You'll be staring at it quite frequently; make sure you love it 👍
