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Advice from: Paul Delury
Condition is probably the most important issue even moreso than the brand. For your first vintage watches you probably don't want project watches that need work, so try to ensure as best you can that the watches are in good operating condition, and check that there is some form of warranty or return privilege if they are not as described. Be aware that unless a vintage watch has had a competent recent service it will probably require a service to clean and lubricate. The watch may not have been used for a number of decades. Pay attention to the visual condition of the movement, (and buying a vintage watch without seeing decent photos is not a wise move unless you trust the seller or a willing to get a nasty surprise). Significant rust on movements is something to avoid. It speaks of moisture ingress and damage may be extensive. Damaged screwheads and scratched plates speak of sloppy watchmaking. If the regulator is hard-over to one side or the other it indicates that the watch at least requires a cleaning/lubrication, and could be indicative of other problems. Cosmetic aging or damage to dials will generally not affect timekeeping, but how much you are willing to live with is up to yourself. I would advise you to look for dials in good condition, as cleaning is often not successful, and you may not be interested in getting redials done at this stage.
Think about the watch case material. For economic and longevity reasons stainless steel is attractive. It weathers the years well, can generally be readily restored, and watches with such cases do not carry the premium of solid gold cases. Gold-filled cases in good condition are fine, but ensure you check the condition. Lookout for wear-through to the base metal, (usually brass), especially on sharp edges and lugs. If the watch has a plated case , (usually gold or chrome), be even more careful of condition. Often the plating is very thin, and thus scratches cannot be removed without polishing through the plating as well. The only practical remedy for badly scratched plated cases is replating, and you probably don't want to get into that at this stage either.
Try to spend a bit of time looking at many different vintage watches before you buy or, if you can't resist jumping in, at least limit your expenditure on your first piece in case you get less than you expected. The more watches you look at, the more able you will be in judging the relative values and condition. Check ebay completed auctions for the type of watches you are interested in. This will show you what they are selling for, (or not selling for!) Be aware that ebay prices will generally be significantly less than the same watches bought from a dealer. However, a dealer may well add value in the form of having provided a servicing, and/or a warranty, which may not be, (and often isn't), the case with ebay.
Unless you particularly like chronographs it may be wise to stick to a simpler time only or time & date style of watch first-up. These will, generally, be less expensive to purchase and also less expensive to service. Keep size in mind also. Many vintage pieces are significantly smaller than modern watches, and so you need to be aware of the physical dimensions.
That said, and off the top of my head, the following wristwatch brands/models would be worth looking at.
Omega - Seamasters, Constellations, De Villes, Geneves
Longines - Admiral, Flagship, Conquest (really, any Longines you like the look of)
Hamilton - Grades 987, 980, 982/M, 770 - all good stuff
Elgin - 21j barrel shaped movements are especially good, Grades 62X, 67X, 55X
Bulova - the 23 & 30 jewel autos are apparently very good
Rado - often chunky styling, but solid watches with reliable movements
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