Buy a set
If you have a thousand dollars to drop, could you possibly spend more? There are some nice vintage sets that you can buy between $800-$1500 at auction (obviously not the highest grades). You get all the cards, and from that point you can cherry pick cards in better grades, or even graded, to update the set. There are a lot of beautiful sets out there, and there are a lot of trading forums on this site to help you upgrade. As you upgrade, the set will gain value as well (although probably not as much as the money you put into it). If it ever comes time to sell, you can sell as a set, or you can do a set break and sell a few cards individually.
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