jtell898

Unless a watch has a reason for being dead at a certain time, I would definitely wind my watches. If one stops working I'll grab another and try and fix it myself, service it, or sell it for parts.

Not only does the Grand Seiko look better, but you better factor that 1700 into your repair costs because 10 years or so in and that Omega might cost you 1700 to keep on ticking

If you're not one to poopoo Quartz, the Timex Q has a great looking GMT at 38mm

That's not normal at all, Rolex will not service a watch that has been.... frankened. They're attempting to sell you unserviceable watches by RSC, I would not buy from there.

You do you but there's no way I'm passing up almost a thousand dollar savings on Jomashop for this watch - a full quarter of the price lopped off. Even if there are issues with availability in your area, for a thousand bucks you could travel to a destination which has them available and get yourself a mini vacation as a side benefit.
Also I recommend trying on as many pieces as you can, all the spreadsheets in the world are no substitute for trying it on exactly as you'd wear it day-to-day. Panerai especially, I never thought I'd be into their chunky style and odd lug protector. But wouldn't ya know, I tried one on and was instantly sold.

I don't double with an Apple watch but I wear a fitbit on my non-watch wrist. I keep it kins busy with various bracelets so it just looks like another one, but I wouldn't choose a tracker with a large face that looked like a second watch; personal preference.

Problem is these things can be so expensive to maintain. If we're talking $100-$200 a year average, what watch do I really want to be putting ... $5k+ in to?
Someone said $1k might be controversial, so maybe I'm super snooty in I think $5k or more, I at least want it to be worth as much as it'll cost to maintain
I also want to make sure the company will still be around next generation. Christopher Ward? Great watches, I like them better than say, Tissot. But if I had to pick a company to choose a generational piece from - I'd have to give the edge to Tissot's longer heritage.

There's tons of intricate finishing above 2-3k, some excellent craftmanship can appear fairly simple if we think machines did it en masse rather than the haute horology brands that do them by hand. The most obvious examples for dials would be enamelling and guioche - techniques so fancy I can't spell either. But they can take a master craftsman dozens or 100+ hours for a single piece.
You mentioned Grand Seikos movement but their zaratsu polishing shows enormous attention to detail and really makes the metal shine.
Then you can get even higher up there where the movement specifically is hand-crafted with some decisions purely being aesthetics over function.
I'm wearing my Christopher Ward #Tide now, it's a very fine, thousand dollar watch. But when I got home, I took off the SBGA435 I was wearing today, now that's about a $9k watch. I look at that 100 times a day when I wear it and usually forget to even check the time. This I just have on because wearing a watch has come to feel more natural than not wearing one. Truly night and day.

My first recommendation if you truly plan to get the Rolex is not to buy an homage in the mean time, you'll never wear it once you get the real deal so you're just flushing money.
If you do, I wouldn't recommend an expensive choice like the Oris. It's an amazing watch on its own, but I have a yachtmaster 40 and I could never see myself wearing the Aquis over it, even though it's gorgeous on its own. I would recommend the Seiko mods that are specifically built to look like a yachtmaster, it's only a few hundred bucks so really you can't lose much when you sell once you get the call.
Something like this you can buy already built for you, or for about his the price you can buy from Ali Express.

No budget? Patek 5231. Sure it'll cost ya 100k, but you can turn around and sell it at any time for 100k so... isn't it basically free?

There's so much black face in this photo I thought I was looking at an old picture of the Canadian PM.

Depends on your budget bud, you could go for the daddy Patek 5231 - won't have to worry about QC issues with them.

For mere mortals Frederique Constant has some cool options with a similar vibe for around $2k and up