Appreciate all the opinions. I took the Panerai, Longines, and new Explorer out of the running yesterday. Panerai was clownish on my wrist, Longines was meh and while I like the larger case, I hate what they did with the dial of the new Explorer, so that is out.
Wrist shots of the finalists:
Mark XVI SpitFire (regular Mark XVI just doesn't do it for me)
Explorer I (no ADs have them, so a DayJust for size comparison)
Portugese Chrono (the auto is more than I want to spend)
^^ hmmm... you have a nice choice of selections but there is some fundamental differences (IMHO) on the styles. Arguably, the port is a dress watch where the speedy is more of a sport. So, my suggestion would be to buy the portuguese AND the speedy.. gives you dress and sport and with some band switching would give you some different looks in between. If I had to choose just one.. the Portuguese hands down .. but only because I love the classic lines and look.
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.
Surely one of them speaks to you - and if its one you've ruled out on price alrerady, then save up for the one you really have feelings for. (sounds simple, but you're overthinking) Dont worry about resale, or even if it fits this purpose or that - you will likely not be done buying watches and if you buy a sports watch and, god forbid, wear it with a suit, you'll be like 99% of the rest of the world wearing Submariners.
My only comment is that if you're buying only one, than your best bet is to go with the one that is the most versatile. In which case, I would choose the Speedy, even though I absolutely love the Portuguese, which is stunning. I've always liked the idea of wearing a watch you can throw on your wrist and not worry about - i.e., jump in a pool, wear to the office, or do whatever else may come your way. The Portuguese is beautiful but delicate and I would suggest that it almost needs to be paired with a weekend watch (kind of like the idea of a winter car to go with your summer car). The Explorer I is also a great watch, but I think you'd get sick of the small size at some point.
So my vote is Speedy or Portuguese, depending on what other watches you have or are planning to buy.