You’re looking at the 3510.50 or the upgraded 3539.50
Now the latter will cost ya about an extra $1,000, if that is a deal-breaker… stop reading and go with the 3510.50
If you want to know what the money is getting you - sapphire crystal, better bracelet/clasp, more water resistance, same movement.
How to tell which if it’s not listed? The cheaper one will have number at every 5 minute hash around the dial, the 3539.50 just has the hashes.

Aren’t redials pretty common in Vintage Rolexes? I’m not sure if I’m missing a joke but would that really drop the value by 75%?

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

Pretty token role for the G shock. With all the options and colors at under 100 bucks beginners can buy in. For the vet they always need something that can take a beating.

As a general rule you buy the seller over the watch. I’m sure you’re getting a sweet deal but I’ve only bought from Dealer’s off Chrono24. The dispute process is lengthy and can tie up your funds for weeks. If you do go through with it, video the package completely sealed and you opening it. I would also recommend you have the ability, or know someone, who can verify a legit Pelagos. You do have time to return products that don’t match the description but again, the process is long.

From a strictly value standpoint it makes a bit of sense. Hard to tell without seeing the exact ROO, but lets say 20k on the Pepsi, 15k on the Batgirl, and 25k on the ROO is I think generous - giving about 60k in value. That aquanaut trades in the high 60s so that would have you “winning”. Problem is that it’s not a 60k watch, and since you’re never selling it then you actually lose the deal.
Definitely would move one of the GMT II’s, you could get an Overseas, might have to add a bit of cash to go blue but it’s worth it.
Patek I would save for their 5231 worldtimer or one of the grand complications. Or I’d go the opposite route and just get a bare bones Aquanaut, maybe an older model, for close to retail

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.

eBay gives you the best protection but they take 15%. Plenty of watches go for 5 figures on /r/Watchexchange you’ll almost certainly need to take goods and services payment and be on the lookout for people looking to scam you, but there is no commission - less paypal fees which can be discussed with the buyer on who covers them. You’ll probably get less than true market, especially as a new seller, but it should be less than eBay’s commission.

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.

Pretty solid deal, buying from AD at prices that rival the grey market.
I would recommend one of the two rubber quick change straps that Oris makes that fit this watch - it’s one of the few that looks better off bracelet.
Now they don’t come cheap, over 300 bucks for the rubber alone, but they can be swapped in seconds and it completely changes the look/feel of the watch. Especially if you go for the light blue strap that comes standard on the sister watch the 75FC.

Since you’ve already gotten advice on the watch itself, I’d say check out /r/Watchexchange where this routinely sells under $2k which should be a better deal even with international shipping and VAT and whatnot

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?

Don’t take offense, but for me it’s kinda… ugly? Sure it’ll be harder to replace, but would you really want to replace it? Explorer II is a true GADA and one of very few watches I could see being my one-watch ‘collection’.

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