Collectible Skateboards?

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I bought a bike from a guy recently that said "I'm not a bike guy, I'm a skateboard collector but this looked cool." I tried to get him to give me a few things to look out for (brand, shape, anything?) as I see so many skateboards at the fleamarket but he was resistant.

So I don't have any idea what the buy/don't buy criteria are but I took a $2 bet on this one yesterday which looks to be in pretty nice shape. Did I break even? What should I be looking out for?
 
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Honestly a varflex with plastic trucks is not desirable.

I’ve been skateboarding for 20+ years, And what’s hot to collectors for the most part is early, early stuff. 70s, 80s. Certain brands of truck and wheels can pull big money too. I’ve flipped a few, and gotten lucky. But mostly because I know what I’m looking at.(just from being around it most my life.) I have a buddy that collects independent trucks specifically (he also happens to skate for them) and the earlier the better. You’re dealing with a product that was essentially built to be destroyed. I’d put it in the same vain as early bmx. People want what they had as a kid, or what they wish they had. As time moves, generations of what’s collected moves with it, but early will always be in demand. (See TOC Bikes as an example)
 

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