Another vote for the Rolex. I have owned five over a long life and not one of them has ever had a problem of any kind. True, they need routine maintenance, but so do all mechanical watches. Read up on the company. They are worthy people who make a superb product.
Wow... lots of Daytona love. But I've never gotten it. (In the 4 months I've actually known what a Daytona is.) I'd go IWC here. Out of that list, it's the one I'd like to have myself.
I'm not a huge fan of the look of the modern Daytona. I much prefer the vintage Daytona's, and if that's the one you were referring to, then that by a long shot. Otherwise, The pre-moonwatch or vintage Heuer would be really cool!
All really different. What are you actually looking for in the watch? Also, you can afford the SMP Moonwatch in that range. Assuming you are like most people here and are quite adverse to dress watches and would rather have 50 divers and 50 chronographs all on metal bracelets, I'd assume the Rolex would be the way to go. :-d
Daytona. The IWC if you prefer something more dressy. If you go for the IWC I would just find one barely used on the sales forums and save yourself a chunk of cash.
I LOVE vintage Daytonas but the modern ones, not so much. The Daytona is a better watch in many regards but I would take a Speedy Pro over a modern Daytona.
IWC - nice, but nothing really outstanding, plus I'm not that much into dress chronos (If I was, it would be my choice however)
Daytona, used - good solid choice, super watch but manages to be "not special" in that group, of the group it will be the easiest to pick up used in the future
Carrera 1153 - the most intriguing watch of the group, IMO, but the case is dated. I couldn't wear it regularly because of the era vibe, but it's pretty 'groovy'!
Pre- Moon - I think this is the winner on several fronts- as a historical (conversational) piece it's at or near the top of ant list. Also, it's styling will likely never go out of fashion. Additionally, wearability spans the range from casual to semi dress better than the others. Lastly, looks like these are becoming to come out of a flat spot pricing wise. They'd zoomed up there late 2000's then leveled a bit but lately it seems to me that they are inching up again and I think that medium or long term gains will be the greatest among the used watches in your group (and the IWC will not let you recoup it price for many, many years).
Unless it's a 60's Daytona, stay away. There's nothing more obvious and overrated than a contemporary Daytona.
When you buy a Portuguese go 7-day auto or 8-day manual. It'd be the best watch of the group by far... but it's not a chrono and the 3714 with its base ETA doesn't have the pedigree (if it was the doppel by Richard Habring that's a different story)...
The c.11 is a legendary movement and buying it in the 1153 is dead-on smart. If you've never seen one in person, wow! Pictures do not do it justice AT ALL. And being the same movement as in the McQueen Monaco... again, smart.
But the best overall watch of the group and maybe of just about any watch, especially took watches is the Manual Speedy.
Make no mistake, this is *only* worth what it's worth because so many of them were made. But the 321 is untouchable.
While Rolex, Heuer, Jaeger, etc we're using Valjoux 72s... The Lemania-based 321 is what the likes of Patek and Vacheron used and still use (in some cases) today...
Speedy is the easy choice, especially with a 321...
Speedmaster professional. It's an icon, can be had cheaper than the Daytona, 42mm looks better on most wrists than the Daytona, iwc uses an ETA 7750. If you want an ETA 7750, it can be had much cheaper than in an IWC.
moon watch for me. i have one and a daytona. the daytona just gets annoying with the screw down pushers. you need to quickly start your stop watch? no probs just spend a minute unscrewing your pusher!
I'd say a very nice reference is the pre-Daytona 6238 and the Daytona 6239... Classic 60's Daytona and no where near as "show-offy" as the exotic dials... not to mention you'll save mooooore than enough to buy the best Chrono ever made, a Datograph
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