Biggest missed opportunity has to be not buying every 1st edition base set booster box in existence back in 1999. I mean I was only 9 at the time… but still.
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Brock’s Trainer Deck A & Misty’s Trainer Deck B about 3 years back, saw them on eBay from $90-$150 each. 
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Three missed opportunities come to mind.
One was when I was younger and I was out shopping with family when we came across this specialty geek store that sold replica/legit movie props but what caught my eyes was the pokémon stuff they were selling (boosters etc.). Turns out that they had tons of single cards for sale as well. They had a special glass cabinet where they featured the more rare stuff they had, and they had lots of Japanese imported stuff. Among some other pricy and rare things, there was a trophy kangaskhan in there as well. It was pretty expensive for a single card (though nowhere near the current prices for a trophy kangaskhan) and because it was so expensive my parents wouldn’t let me buy it.
The other two were more recent. One auction of I believe 7 sealed base set 2 booster boxes and a starter kit box on yahoo japan that sold for a very good price. (what the heck were they doing there on yaj?)
And one other japanese auction with all Japanese shinings, crystals and a ton of gold stars that basically sold for like 25-30 euros per card if you were to divide the price evenly among all cards.
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My whole life
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Not so much a missed opportunity but a nagging thought. When I bought my trophy Pikachu with cullers when the set was being sold last year I went for the no. 1 trainer. when looking at the art over this time I’ve grown more fond of the idea of the fat chu on the no. 3
Possibly a case of “want what you can’t have” but I’m surprised how the thought sometimes recurs
That’s why I got all 3!!! 
lol
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some day my friend, some day
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Got offered a PSA 10 Legendary Collection Reverse Charizard for $450 and a PSA 10 1st Ed Shining Gyarados for $500
from 2 different sellers. Declined both thinking they would go a little lower but nope, both cards sold before the
the day was even over.
I’m really worried they’ll skyrocket in price like 90% of the other cards I wanted for my collection.
Whenever I think of the opportunities that I missed out on, I just think of the fact that I definitely used that money towards some other collection goal that I probably would have kicked myself for not picking up at the price that I did at the time. Always puts things in perspective a bit more and I feel a little less awful.
Except for the $500 1st Edition Neo Destiny box I passed up on. I still wake up in a cold sweat over that.
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i managed to get that and then sold it 1 month before pokemon go came out the worst decision i have never had
You bought that guy’s set? You were trying to sell me a Japanese set for a bit. I didn’t know you had that one.
Newly identified missed opportunity: Team Rocket Special Case Promo haha
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Just got outbid by a dollar because my eBay app crashed…26$ for 3 cards worth 25$ each…
Psa 7 first ed shining zard bin for $70.
Thought about it for 20 mins as i was going for a better grade or raw (long time ago).
Decided to go for it and it was gone. Still havnt bought one as i cant justify paying the price for one now. Id rather buy something more fun, like a spear gun
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www.elitefourum.com/t/mitsuhiro-arita-special-guest-1st-european-partecipation/15386/1
Literally saw this 1 hour ago and realised the submission was closed on the 15th of Feb
Wanted to have my unlimited and evolution charizards signed because I need the sensei’s signature on his signature artwork in my collection of original artwork charizards. Well maybe one day I’ll attend a Pokemon event and hope that he will be there signing for fans. Still can’t get over this
EDIT: Just realised you said Arita haha. Nevermind ignore me. I wish I could meet him too T_T .
I was one of the lucky 100 that got to meet him in Tokyo last November when he was signing the new artbook. I pleaded with him to sign the FA promo as well but he said no T_T - but I still got him to sign my book so not too bad haha.
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To add to the missed opportunities though - I remember taking a day off school back in 2010 when we had a GAME on Oxford Street (London) to meet Ken Sugimori and Junichi Masuda for the BW game release. I got them both to sign my, my brother’s and my girlfriend’s DS. I didn’t think about cards back then, but they had the blister pack with the Arceus charizard at the front. Bought it and got sugimori to sign it. I’ve always treasured the card since that day, but how I hate myself for not bringing in one of my base zards, or you know, any card that he actually designed haha.
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Japanese Grand Party card for £30 nm/m, I didnt miss as such…He sold on ebay before invoicing me via paypal.
Pretty gutted though, I really want the card! Its quite expensive for myself though, psa graded 
1st world problems!
Pretty obvious but in general: **legit** sub-$1000 Shadowless Base Set Booster Boxes less than 10 years ago. 