A quick trawl through Ebay at your pricepoint brings up loads of basket cases. There may be a diamond or two in the rough out there (even if most seem to be quartz), but it will probably be a long and tedious process finding one. If your budget is $300 all in and you have not factored in the cost of a service than your options are even further limited.
Perhaps you might consider casting your net a bit wider than Omega. For a modern "vintage" looking dress watch, the Orient Bambino is hard to beat.
http://www.orient-watch.com/products/category/item/?category_id=145
Or maybe keep an eye on the sales section of this forum. Generally good quality at reasonable prices.
Good luck finding something that satisfies you
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