It's pretty shocking to me that I can't think of a grail watch. I'm just enjoying my watches and don't have a super strong desire to upgrade/attain at the moment.

Here is my v1 after 3 years of natural patina. Nice gradient effect. Looks almost like the pull up effect on Horween leather. 
 

It‘s interesting that you mentioned you prefer the 60 click bezel. The v1 does have a 60 click but the problem is that as a gmt bezel, it is not possible to align the odd numbers on the bezel with the dial indexes. So  the  60 click bezel on the v1 Is not all that useful for gmt function, but it has great action though, and makes for a fine timing bezel. 

I gravitates toward sportier watches, so I'd spend the bulk of the budget on an Omega SMP 300m in forest green, on the rubber. I choose the rubber option because if you put resale value aside, the rubber version is the version to get because it is very comfortable especially compared to the chunky bracelet. $5000.

My second pick is the Damasko DS30 on submarine steel bracelet. At $1500, this watch gives you an indestructable vibe for not a lot of money. Yet it is a very versatile watch for any occasions.

With my staple pieces out of the way, I'd venture for something fun for the third pick: A manual wind, panda chronograph from Lorier at $500. It's just hard to argue with the look and the price.

Cutting real close to the budget with these 3 watches, and I don't think I can afford to pay the sales tax on these. 😕

Love them!

I see words like "DONE" or "Exit Plan"... 

If you go on WebMD, the utterance of these words are literally symptoms a condition known as watch addict denial syndrome. Let's face it. And you know it. 😭

I think you can justify it either way, so a fair trade in both directions. 

I personally would go with the air king just because I prefer simple luxury and no one does simple like Rolex. Take the bracelets of these watches for example, they both look nice enough in photos, but you'll find the Rolex oyster bracelet is quite a bit better when you handle it in person. 

If this is your 12th watch and you've got some other staple pieces already, and you are looking for something a bit more niche, out-there and exciting, then the Zenith makes a lot of sense. It's a good looking watch. I personally, wouldn't go with the Zenith though in this price range, as I find a GS 5-day spring drive for example, as a more fundamentally interesting watch as far as movement goes, if I'm looking for a watch with an interesting movement. Then again, don't listen to me, because you're not me. :) 

That GS spring drive is probably my fav in my collection right now. Cheers.