Great thread!
TLDR: Collecting consistently since Summer 2019, but I have collected on and off since WOTC.
Pokemon has been a part of my life on and off for many years. I flip flopped between the games, the tcg, the tv show as well as other hobbies. I was particularly fond of Yu-Gi-Oh for many years. I collected a lot of cards from the original era through the beginning of 5Ds. There were also some Legos, Star Wars Figures, and Nerf Guns thrown in. There were multiyear gaps with no Pokémon followed by brief bursts of interest. This was my collecting journey until Summer 2019.
My earliest card memories are with Wotc. I had cards from the first half of wotc, although I don’t remember ever opening up packs to get them. I have some cousins that are a couple years older, so its highly likely that some of their cards made their way to me throughout childhood. I recall opening up something outside of a 7-11 of all places. I wanna say it was a base set pack, but it could have been one of the Machamp starter decks for all I know. I remember something blue 
That is probably my earliest Pokemon memory, but there are other moments where I remember cards, such as sitting on my room floor with dozens all scattered around. I was only a few years old, so its no surprise I can’t place events in order.
Anyways, sometime around 2007, an older cousin gifted me a bunch of his cards that he didn’t care for anymore. Most of these cards were from the later ex era sets, with a few dating back to early wotc. The ex era ones would become my most cherished cards and would help solidify my love for all things Gen 3. The set stamps were my favorite part of the cards. He had a quite a few ex pokemon that made it into my collection. The only ex era product I remember opening was a Dragon Frontiers Feraligatr Delta Species theme deck!
I was really drawn to the delta species cards, particularly the dual steel type ones! I’m sure that I opened and pulled some these cards, but I have no memories to prove it! Here are some of the cards that I really liked from this point in my collection history:
My memory gets a lot better once we get to DPP. I’ve opened just about every DPP era Lv. X tin, and still have most if not all the promos in my collection. Every time I went to Target or Walmart I was always asking for one of the “$20 tins”, and often used what little money I had to buy them. Only recently I learned that many of these tins were likely under that $20 price tag (it was a low point in Pokemon after all), but I will always think of “$20 tins” when I see a Lv X promo. I remember seeing bunches of Mewtwo and Charizard Lv. X tins at Target/Walmart, as well as tons of the starter evolution tins.
It was around this time that I developed a fascination with the HP of a pokemon. I had no real grasp of what a “set” was, nor what “secret rares” or “chase cards” were. To me, the “best” cards were the ones with the most HP. It’s funny to think about now, but I was more excited back then to pull some non holo with 100 hp, than a holo with less than that. I remember trading away a Neo Genesis Lugia to someone at recess for some random card with 100+ hp. This was obviously a great deal on my part, as Lugia only has 90 HP 
Outside of this trade and another that also involved a Lugia, though this one being the Pop series 5 one, I never got rid of any cards. I’ve never sold any cards and don’t really plan to. I have lost quite a few though.
The last product I remember opening from this era was the Jumbo Arceus promo collection box. Funny enough, I really didn’t care for it! I didn’t like the jumbo and it seemed awkward trying to find a place for it. Its long lost now, but still nostalgic for me.
Here are some of my favorite cards/products I remember opening from this era:
It was the end of Platinum era that saw a long gap in my collecting history. While I have some cards from the HGSS sets, I have no memory of pulling them, nor any strong connection to the sets like I do for DPP and ex. I did purchase Pokémon Black for Nintendo DS, but I had no interest in the cards. For many years I really didn’t care about Pokémon. I was more focused on playing Call of Duty to be honest.
During high school I got into the Pokémon games again. This reintroduction was spearheaded by my love for ChuggaaConroy’s Pokémon Emerald playthrough. I was (and still am) quite a noob when it comes to the Pokémon games. His playthrough of Emerald really captivated my attention, mainly due to his in depth bios for every single Pokémon. I learned so much about the games from him, and spent the next few years playing emulators. My favorite game to play was Emerald, and to this day it remains my favorite of all the games. I have a connection to the cards from ex, the games, as well as the tv show/movies.
While I was back into emulated games, I didn’t get into the cards until 2019. I don’t remember which video it was, but Youtube recommended me a video from Unlistedleaf. In this video (or videos?), he opened up Skyridge booster packs, as well as a bunch of other wotc sets. When he explained how expensive Skyridge packs (and even the empty wrapper!) were and how rare and sought after the set was, I was hooked. The thought that I may have cards actually worth something was a surprise, as Pokémon was still pretty unpopular amongst my social circle and the internet in general. I didn’t play Pokémon GO and hadn’t bought any cards or main series games for many years.
I still had very little understanding of what “rare cards” were and what made certain cards sought after. Nonetheless, I started watching more Youtube videos of people opening packs. I soon found Maxmoefoe and proceeded to binge his channel for several months. During the summer, I had a student job which would inevitably fund the first card purchases I had made in around 10 years. I went to Target (the best retailer for Pokémon imo) and browsed their selection. I don’t remember much, but I ended up buying a Charizard EX tin (since it reminded me so heavily of the Lv. X tins) and some Burning Shadows packs. Another purchase near this point was the Kanto Mini Tin set. I loved the design!
Hidden Fates was the first set that I actively looked for in stores. I remember driving in the rain to multiple Gamestops trying to score some tins. Black Friday 2019 was crazy. I remember seeing dozens of Hidden Fates tins for half price. At the time , I ended up buying about 10 tins, half of which were non Hidden Fates tins that I thought may have some cool packs inside. In hindsight, it wasn't the best decision. Had some very solid pulls from all the Hidden Fates I opened, but never did get the Zard... Here are some stuff that I pulled from my initial purchase of tins around Hidden Fates release. The Black Friday print seemed pretty low on the rates compared to the initial print, but who knows. I seem to remember pulling at least 2 hits per tin at release.
It was also around this time that I had the genius 
idea to go and buy as many McDonald’s toys to try and pull all the cards from the 2019 set. What could have been a simple $20 ebay purchase turned into a multi day scramble to hit up each Mcdonalds. I did end up getting every card, and still have all the duplicates. Looking back I cringe a little thinking of what it looked like to ask Mcdonalds employees if I could buy a dozen happy meal toys. Live and learn I guess… This was before the crazy hype of 2020/2021 and the infamous Mcdonalds 25th anniversary debacle. I think I’ll pass on future McDonalds sets and just buy the singles on tcgplayer. The last card I needed for the set was Alolan Meowth.
I spent most of the money I had made during the summer on Pokémon, and had pretty much run out by the end of the year. I started thinking a bit more about what I was actually buying. The Mcdonalds and Hidden Fates hype was so much fun, but now I was thinking back to my childhood cards and collecting goals at large.
Fast forward to late February/Early March 2020. I bought a few cards on trollandtoad. This was the first time I had ever bought singles. Looking back, I think I made some big moves 
The Aerodactyl was one ex era card I always wanted. I love the art style and I was so happy to find it for a reasonable price! I have a Pokémon guide from 2004 that has a bunch of high quality scans of cards that I would stare at for hours. On one of the pages lay that Aerodactyl. It’s neat to think that over 15 years later I would purchase it. The book prices are not that accurate now I’m afraid.
I made my first in store singles purchase around this time. I remember going to a local comic book store on Friday the 13th, the day that the world turned upside down in the US. Throughout the rest of 2020 I started watching more experienced collectors, namely TCA Gaming. It was through his videos that I learned more about grading, what “WOTC” was, set names and structures, the market, and many, many error cards. While the world was closed down, I binged Pokémon content. It was around Darkness Ablaze that I started paying more attention to the market and what upcoming sets would contain. I would preorder some of the new sets, buying singles every now and then from Tcgplayer. I spent a whole lot on Shining Fates and Celebrations, pulling most of the chase cards from each set.
I still consume lots of Pokémon content daily and have many goals that I am working towards, albeit with a bit of a pause until I get a nice job going 
I joined e4 in the last year or so, and have come to know a lot of the higher end collectors and many unique cards. I still am very much in tune with what goes on in the Pokémon world and devote too much time to it if I have to be honest. Still, the hobby brings me so much joy and has certainly made the last few years very special. I feel I got in to the hobby at just the right time. I’m really looking forward to the rest of this year’s releases. Scarlet and Violet look super promising. I hope the SCVI era has more surprises in store. I feel Sword and Shield has been the best era as far as modern is concerned. So many cool products, sets, and cards still to be enjoyed.
As far as goals go for this hobby, my main one is to simply have fun. One of my favorite parts of collecting is learning about new cards and revisiting old favorites. There is so much fun that can be had for under $100 and the wealth of free knowledge is insane. I hope to complete some Wotc sets in the future, purchase some alt arts, and buy as many ex-dpp cards as I can.
), and it’s my favorite card from the Jungle set. The Snorlax I traded for a WB Mewtwo promo. The trade wasn’t too bad at the time, but now it would be a very, very bad trade.
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I’m trying to start getting into CardMarket more though as it’s Europe based.
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I wanted to complete the set, but to this day, I haven’t quite… a few holos missing… Anyway, that’s when I started selling too, to get some money back from that skyridge box, but I’ve never been a big seller. So, all in all, I’ve been in the hobby since 1999-2002, then from 2006-now, and around eBay for 15 years.
