Hey Chris. Yeah, I live in CA. I really like the vintage watches from the 50s/60s, in particular the Omegas. I just really like the look of them. I googled vintage Omegas and most of the results were watches listed on Ebay. From what I have been reading on this forum, however, it seems like many, if not most, of the Omegas listed on Ebay (and other vintage watches for that matter) have issues which to a novice like me would not be obvious. I can talk to you about first editions and antiquarian books for days, just because I have been collecting for 20 years+, but when it comes to vintage watches, I am pretty clueless. My concern is, if I spend $800 - $1500 for a vintage watch, I want to make sure that it is right and that I am not spending $1000 for a watch that in reality (with condition issues) is more like in the $300 range.
I know that people have recommended just going through the marketplace on this forum, albeit just from browsing the first 10 pages or so, many of the watches listed for sale are not Omegas and of the Omegas, many are diver watches and more modern ones.
There was a point where everyone wore a wristwatch. They were a necessity, not an affectation. Many owned more than one. As a result, there are literally millions of vintage watches out there. What isn't out there are millions of good, original, well-kept, reliable watches. Everyone here is looking for those perfectly preserved or nicely aged and patinated examples. Welcome to the race.
Now, the thread has focused on value and prices. So it's worth thinking about how a watch (or anything else) is valued.
Of those millions of watches that were made, some were cheaply made, mass produced and will always be cheap and mass produced. That doesn't mean to say they don't have some appeal. Some of them had a "look". Some have aged well.
This Smiths, for example. A solid 15 jewel movement; a brand with some pedigree; interesting story to the model ... and a usable one will be less than £100 with a very well preserved, serviced, example like this one still under £300.
There are plenty of watches available in that price range if you're willing to compromise on things like dial condition. You should be able to find all of the ones below in the £200-400 range. At this price, you really should expect to have to pay for a service and will most likely find the crown has been replaced. It may be a period correct replacement but most likely won't.
Now, you've said you're specifically looking for an Omega. Believe it or not, you can still be in the same ballpark ... but you can also move up to the next level. What will determine the price point is condition, authenticity and desirability. Everyone is hunting for their own unicorn but some of those unicorns have more people chasing them than others. Fortunately for you, those Omegas from the 50s and later are still relatively plentiful. What is more plentiful are those watches in poor condition. It takes little work for an unscrupulous dealer to turn an £80 piece of broken down crap into something that looks (at least to the unsuspecting novice) like a £1500 gem. Pricing that at £800 on eBay makes everyone happy ... at least in the short term. The only way to know the difference is to study: read; look at photos; and, most of all handle as many examples as you can. You've already been directed to the "how to fish" post. READ IT. Learn it.
Your $800 budget can get you a very passable example ... but not from a dealer. To get a good early Seamaster (for example) in that price bracket, you're going to have to put in a lot of leg work. I go to 6 auctions a month; I have standing searches with auction houses; eBay; watches on and the like and in the last year, I've bought these two (on the left):
Far left is a 1949 2581-1 in stunningly original condition; centre is a '53 Seamaster with a hobnail dial that's almost as good. Both cost around £7-800 and both required a service and at least one part for the movement. You're not going to get these from a dealer for less than £1350 in fully serviced condition (though you will get a warranty too). To buy from auction, you're just going to have to put in the time and have access to a good watchmaker.
Your can also do what I do ... and buy them straight off the wrist of their current owner. It all depends how personable you are and whether you mind being told to .. Go away.
(Though that last is a far bit beyond the budget you've mentioned).
Good luck in your hunt. That's where the real fun is anyway.