re: Watch Service - How Often and Where?

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After watching the detail the factory goes through for one of their $700+ services, I would be willing to pay it... but maybe not every 2-3 years

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That is a Seamaster 2254. It, fortunately, has the Omega caliber 1120 movement. I say fortunately because it doesn't have the 2500 movement which was coaxial and the early ones were known for having issues. The 1120 is based on the ETA 2892-A2 so it is a solid workhorse that I am not surprised started right up.

Worn daily that movement is good for 6-8 years IMO between services, but it needs a service now to get it properly oiled and get it back running within COSC standards.

Given the rather ubiquitous movement in your Seamaster, you don't need to search out an Omega whiz. Watch Repair on Florida if you are in BR and want to keep it local. My Omega's either go to Archer Watch repair in Canada or Nesbit in Seattle. Al at Archer is one of the premiere Omega service and repair guys in the Western Hemisphere but you don't need his level for an 1120 service and I don't know if he is even taking work from new clients now, he has a following.

To use a watch winder or not is an age old question. I do not use winders but my watches get worn about 1 day every 2 months. My general recommendation would be to use a winder if you wear the watch most of the time and just want to keep it running for the few days at a time you don't. If you only wear it a day or two every couple of weeks then I would avoid the winder and just pull the stem so it stays wound and set it each time you wear it. This is what I do for my watches that hack. If you do get a winder make sure it is set correctly for the 1120 movement (the same as a ETA 2892) which happens to be both directions and 650 TPD (turns per day). You don't want to overwind as it just adds needless wear.