I realize I am basically looking at 3 sport watches and 1 casual-capable dress watch. While the Portugese line is the first that I can remember loving, the big brother auto is the one I really love. The reality is I will never spend the money for it and it looks like an oreo on my wrist. The Port Chrono would be PERFECT with the auto's subdial placement.
The Mark XVI perfectly straddles the sporty/dress-capable line IMO. The big drawback is that while I have no intentions on selling down the road, I very well could, and I basically see no one else interested in this model, so I would probably take a bath on it. I also think it is overpriced even with a good AD discount, and have yet to see one come up for sale in the used market.
The (old) Explorer is a winner in every way except case size. I don't like the Explorer II, and I don't want something as obvious and commonplace as a Submariner.
The Speedy is terrific, classic, but is also the most sporty and not as versatile to me. While I love its looks, it (IMO) does not look like a 4k watch.
I know this isn't the intent of this thread, I'll take my decision process offline, thanks.
May I suggest a new contender: the Blancpain Aqualung. It looks very similar to the Explorer, with the added benefits of a larger case size and date window. The older version that I own is 38 mm with a small date window. The newer version is 40 mm with a big date window.