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I would like to add to my son's large collection of first generation WOTC cards issued 1999-2000. I know nothing about which cards might be a good choice to add to his collection. I want to stay in the WOTC series and have been looking at Promos & PreRelease & 1st Editions & Gold W cards. Would someone please help me understand which would be more desirable. Thanks!

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1st Editions are generally more desirable, so I'd say you get those. There is one 1st Edition in particular, Machamp 1st edition which is not very desirable as it was mass printed in a theme deck, I think. I don't know much about prerelease or promos, but I know one pre-release in particular which was pretty rare, its the Raichu Pre-release card, WOTC denied its existence for a lot of years.
One promotional card which is very rare is the Illustrator Pikachu, as far as my memory goes- I think the Birthday Pikachu is pretty rare too. I'd suggest you go to a Pokemon TCG subreddit on reddit and ask questions over there: Pokemon TCG subreddit

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collecting also other cards would be cool,like the flying or surfing pikachu.

getting into the whole card collecting in the side of Pokemon is fun.especially when you have protectors of colors and glittery ones and binders to create a cool looking collection,shinies or holos are a cool adittion too to the whole collecting bizz.its a nice hobby aswell.

though,dont let yourself be eaten too much by the promos or editions or event cards.as this side is addicting,so there has to be a limit.

but overall,itd be a good hobby,as I myself used to collect alot of the first gen cards and second gen too,still holding on to my first promo card of mewtwo from the first movie.

im sure all 4 of them are desirable,but have a limit okay?

collecting in ebay and amazon and other places are also a really big hassle as buyers arent willing to buy a one card of an eevee for just 1,000,000$

but its funny to laugh at that too. so yeah,its all good.

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