Hi Orion and good luck! Here are my thoughts for what they're worth as a relatively new (4 years) Omega collector. Your tastes are likely to develop and change as you see and learn more, and you want your first vintage watch to be a friend for life, so classic simplicity is probably best. Obviously where you live will affect your choice - much greater in the United States than the UK for example. It also depends on your budget. If I were advising myself four years ago, I'd say go for the 60s Seamaster and Seamaster De Ville range. Be very patient and very picky buying your first watch. My choice would be a 552 or a 565, but I like autos and there is nothing wrong with eg the 601. Avoid black dials at first - the one you linked to is a redial [edit - I see that's been posted while I was wirting this], and real black dial 60s SMs are extremely rare and thus suspicious. There are good sellers in the more exotic countries; there are also quite a few bad ones and it might be best to play it safe. Always scrutinise the hands - is the tip of the minute hand level with the minute markers? Do the hand colours match the hour markers? It's very nice if you can find an appealing feature like cross hairs or a linen dial. Spend some time searching ebay completed listings. A good tip is to arrange them in price order, low to high. When you finally buy your watch, it will need servicing and you should budget for that. Resist the temptation to wear it unserviced as you are likely to cause excessive wear and damage. Finally, wear the watch, learn from it and take your time to decide what you want next.
Here are some examples of recent ebay items I think were a good deal. If I've made any glaring mistakes, which is very possible. hopefully someone will point them out.
http://www.ebay.co.uk/itm/Vintage-Omega-Mens-Automatic-Seamaster-De-Ville-Wrist-Watch-Silver-Black-NICE-/371688877476?hash=item568a622da4:g:ChsAAOSwqfNXj8sg&nma=true&si=CroZVRpBRqz9PdZpK6N%2BRXR7%2FDw%3D&orig_cvip=true&rt=nc&_trksid=p2047675.l2557Purchases made through these links may earn this site a commission from the eBay Partner Network
- not exactly exciting but nice, clean and a good price. Has the correct crown. A budget classic.
http://www.ebay.co.uk/itm/Omega-Seamaster-De-Ville-Vintage-1962-Manual-Cal-601-Case-No-135-020-/142024154530?hash=item21114c9da2:g:8SsAAOSwGIRXXv-U&nma=true&si=CroZVRpBRqz9PdZpK6N%2BRXR7%2FDw%3D&orig_cvip=true&rt=nc&_trksid=p2047675.l2557Purchases made through these links may earn this site a commission from the eBay Partner Network
- stainless manual 601 in very nice condition, with cross hairs and correct crown.
http://www.ebay.co.uk/itm/Vintage-OMEGA-Seamaster-De-Ville-Automatic-Waterproof-Watch-Swiss-Made-Working-/121980986287?hash=item1c66a223af:gqoAAOSwt7pXL9n6&nma=true&si=CroZVRpBRqz9PdZpK6N%2BRXR7%2FDw%3D&orig_cvip=true&rt=nc&_trksid=p2047675.l2557
- a good value SM De Ville. Correct crown. Glass scratched but dial seems good underneath it. Apparent discolouration at the foot is probably a reflection from black tape on nasty bracelet.
http://www.ebay.co.uk/itm/Omega-SeaMaster-Automatic-Watch-570-Stainless-Steel-Case-Serviced-/131816941185?nma=true&si=CroZVRpBRqz9PdZpK6N%2BRXR7%2FDw%3D&orig_cvip=true&rt=nc&_trksid=p2047675.l2557Purchases made through these links may earn this site a commission from the eBay Partner Network
- not as cheap as the others but to my mind a thing of beauty with a superb linen dial.
http://www.ebay.co.uk/itm/Omega-Seamaster-cal-354-/182179993131?hash=item2a6ac6162b:g:4kEAAOSwOVpXaiX1&nma=true&si=CroZVRpBRqz9PdZpK6N%2BRXR7%2FDw%3D&orig_cvip=true&rt=nc&_trksid=p2047675.l2557Purchases made through these links may earn this site a commission from the eBay Partner Network
- very cheap with nice case, nice correct crown and guilloche dial. I don't know why this didn't make more, have I missed something? Depends on whether you can live with the faded dial.
Finally, here's my £128 552 Seamaster from eBay UK 3 years ago. I had to add the BOR and of course service it, but good deals are still out there if you are patient, diligent and lucky:
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