Overall I’ve been really lazy seller through the years, however now when I look back I should’ve kept english PSA 10 EX Holon Phantoms Pikachu gold star. Found it for very cheap price and used Ludkins middleman service for grading, those were the good old days. 
I got back into the hobby in 2015 and wanted to reignite my interest so bought a whole bunch of 1st edition rocket and jungle packs to open. I think I pulled one holo from about eight packs as most were weighed.
I don’t really sell my Pokemon items but wish I kept them sealed or put that money towards something bigger when 1st edition base set was much cheaper! (At the time I thought it was crazy Charizard was so expensive, if only I knew what was coming)
Sold/traded most of my mint gold stars around 2009/2010 
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My dreams.
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I regret selling everything in the past that had the word “Pokemon” or “Pocket Monsters” attached to them.
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isn’t there some sales philosophy… that goes, ‘almost every sale you do today, is bad when you look at it in the future.’
i don’t know the exact wording…
but yeah…
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1st edition base sets complete 102/102 nm+ $600 aud… 2 TIMES!!! i sold them that low…
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FREE PRE RELEASE JUNGLE CLEFABLES! GIVEN AWAY in jungle sets… multiple times…
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Just so much stuff in general is being flipped from me, i actually don’t mind now… but once i sold a jumbo tyranitar plush for 1.2k and the week after was on ebay at 2.5k by the buyer who won it…
sometimes it’s frustrating. but it’s a trading card game after all… so i guess its meant to be traded? and if i can make my money at the time, or make someone else happy, i’m happy. and if people can make money on top of what i’ve sold, or trade abroad from me, then i’m happy for them as well. everyone wins.