re: Could you help w/ a watch decision

Neither.

Buy a Tag or a nice Seiko and put the difference down on your mortgage.

But hey, that’s just me.

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Omega is a working man's Rolex imo, Rolex is more for show than wearing especially with the mark-up on them

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That is an opinion I just can't agree with. If you remove cost Rolex makes arguably the best daily wear mechanical watches of any manufacturer. If you ever strip-down (or see one stripped) a modern Rolex movement and you have a good frame of reference the terms over-engineered and over-built will almost certainly come to mind. The cases and particularly the bracelets are simply at the top of the game when it comes to daily wear robustness. Even considering cost and making the argument they are too expensive to wear daily one shouldn't forget for a few hundred dollars they can be returned to like-new condition. Like most watches, you could take a 50-year-old Rolex daily wear watch and restore it to as good or better condition than when it left the factory although it would cost more than a few hundred bucks and no sane watch person would do it.

Now it may sound like I am a Rolex apologist in this thread but I am really not. I just take issue with opinions of Rolex that aren't based in fact. My timbre on watch forums is much different because most people there actually understand that Rolex makes an excellent watch at or very near the top of mid-range watches. I like Omega essentially as much as Rolex and have roughly the same number of each in my collection. I really like the Omega 8XXX and 9XXX movements but I am just not as high on the 1861 chronograph movement in the Speedy Pro. It is just that I prefer column-wheel chronograph movements to cam-operated ones. The original Speedy Pro came with the Lemania 2310 aka Omega 321 movement that was column wheel activated it was changed in 1968 to the 861 movement which is cam-actuated, it was done for cost and ease of manufacturing to keep up with the demand due to the attention it received from its connection to NASA.

If I were buying a new Moonwatch today I would make sure it is the newest 3861 movement even if I had to wait. It is Master Chronometer/METAS certified so it will be more accurate. Has hacking seconds. It has a free-sprung adjustable mass balance with a silicon hairspring. It can resist magnetic fields of 15,000 gauss and will resist shock better, be more stable with temperature changes, and have better rate stability over time than the 861/1861. It is still cam operated but many watchmakers will argue a good cam chrono is as good as a column (castle wheel) movement, but I am a column wheel snob and prefer the pusher feel.

Neither Omega or Rolex are the be all end all of watches but they both make excellent mid-tier watches that can last well beyond the initial buyers lifetime if cared for properly (but no need to coddle them). The biggest difference is the Rolex will cost more upfront but will retain more value.

Again if it were me and it was to be my only watch I would get the OP but in the dark blue dial and call it a day. If it is in a rotation of watches I would need to know the other watches to give an opinion.

Speedmaster, very common watch and will be easy to unload if you want to sell.

Rolex dial, well... Not my taste.

That omega speedy will be a gift to myself some time in the next 5-6 yrs. Absolutely love that watch,

Hey Obtuse, what is your opinion on Bremont watches?

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The Omega is more versatile, that would be a big factor in my decision.

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I think the Speedy Pro is a great watch and it is one of two Omegas I own, the other being an SMP Planet Ocean, but a chrono dial is never more versatile than a time only dial. Certainly better for some specialized functions, but not a wear anywhere w/ anything type of watch.

Unless you are in a smaller town or have a good relationship with a Rolex AD, you may have some trouble getting your hands on an OP 41. Likely will have to go through a broker and right now those are trading over retail.

I have a white dial (actually looks silver) Oyster Perp 39 mm that I enjoy. Simple, goes with a lot. Won't depreciate a huge amount in the short term if that's important to you. Are you looking specifically for the dial color in the pic.

I will ad the disclaimer that I'm going to more or less always pick Rolex over Omega, and I would tell you to do everything you can to not pay retail for an Omega, but you probably know that anyway

Of those two, the Speedmaster. But keep in mind the Speedmaster is a manual (hand-wind) movement. So there is going to be more "work" involved.

Recently I was between the Speedmaster and a Seamaster 300 (not 300m). I ultimately went with the Seamaster in part because I wanted a diver a bit more than a chronograph, but also because I was hesitant of dealing with the daily pain of having to wind the Speedmaster. Still, the Speedmaster is an icon I may get one day.

That said, the Rolex is great too (just not that dial color for me)

cracked the ceramic bezel on my sea dweller. $1200 to repair. I have a tough time justifying it, but it is the last piece of jewelry a man can wear besides a wedding ring.

I would go with the Speedy fer sure in that decision.

Rolex. I absolutely love my OP