I have just recently got back into Pokemon and am interested in starting my own collection.
I have a separate investing that I do, so this will be mostly for collectors standpoint, however looking for future potential would be nice also. I done some research and watched some youtube but still having hard time which generation to start. I know that I want to buy some booster boxes as well as elite trainer sets to keep it in my collection (possibly other etcs.) So my questions is which set should I start my collection with to have a good base and is still worth buying despite most of the older generations having higher price. Any advice or guide would be great. Thank you
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Collect what you actually like and the rest will follow. Everyone is going to have a different definition of whatās āworth buyingā. Youāll enjoy your collection and the hobby as a whole a lot more if you collect what you personally like.
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This question is unanswerable. The best advice is really just to buy what you likeā¦ do you want to prioritize early cards, do you want to focus on a special set of rule cards (ex, delta, V, GX, etc.), do you want to collect only english or only japanese or both or all languages, do you want to make a profit over everything else? Thereās a million more questions that have to be factored in to what you want to start in. Iād start looking over the sets here and just see if thereās anything that really catches your eye
www.pokellector.com/sets
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Well, the first elite trainer box is Plasma Storm, so you could always start there. If youāre collecting simply to collect, buy what makes you happy as otherwise is there really a point to collecting? 
As long as you are patient and donāt āoverpayā for items regardless of generations Iād say youāll be good. My only recommendation is to buy one thing that is āexpensiveā in relation to your budget rather than a whole bunch of ācheapā items. @jmin1231, & welcome to E4
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Suggestion: Make sure to check out pkmncards.com. See what cards intrigue you and start with the corresponding set. This is both collectorās and investment advice. If you collect what you like, you will stay in the hobby longer. And from my experience, if you like a card, chances are others like it as well.
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VS is a good set to collect because all of the cards within the set are Japanese -exclusive. This allows it to tick two boxes 1) every artwork on every card is unique 2) the set is still somewhat flying under the radar considering itās release year so you could finish this set before it gets too expensive.
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I agree the set is phenomenal, but itās pretty darn expensive already. Every card seems to go for 10$ minimum unless you catch one for bid. Thatās coming from personally selling almost the whole set for those prices and higher over the last few months. Not to mention the trainer TMās can be surprisingly tough to acquire. Even living in Japan it took me time to piece it together individually.
Ultimately, like others have said, buy what you like. If it drops in value, who cares. Chances are, if you like it, someone else probably does too. At least thatās how I tend to do it and it works out for me in terms of loving my collection and investability.
What era did you grow up with personally? Which cards/PokƩmon in general give you the biggest burst of nostalgia? I think these are the questions that ultimately will tell you where to start.
If itās from a collectorās standpoint rather than investment then collect the cards or sets which bring you the most feelings of Nostalgia, for me the older sets and unnumbered promos is where I based my collection, every now and then Iāll stray to a newer promo and whatnot but my main collection is on cards made before the 3rd generation of Pokemon started.
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I used to believe in the ābuy what you likeā saying, but Iāve seen what some of you like, sheeesh
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Yeah, some people like Japanese over English 
Iām not seasoned on this forum, but what I can tell you is to try not to buy everything that slightly piques your interest, especially if you donāt have a lot of capital. Donāt buy something because you feel pressured to by what you see on social media. Go after cards/items that you REALLY want so you donāt find yourself not having the capital when a card/item comes by that you just have to have. Evaluating What you āreally wantā can be a slow process and can be difficult when youāre just starting. I suggest taking a long look at sets to see what interests you the most (thereās a āPokemon Priceā link at the top of the forum that can take you to a site that has complete English Pokemon sets and historical sales data).
I also suggest doing your research on population reports and to avoid buying modern chase cards that released not too long ago - their prices will decrease/stabilize as more are sold and graded. Additionally, modern cards are just easier to grade, so higher grades wonāt be hard to find.
āBuy what you likeā, lol. Might as well lecture people on how to breathe while weāre at it. Everyone entering the hobby with some interest beyond pure finance is, per definition, going to ābuy what you likeā. Everyone with any concern for their financial welfare is going to attempt to buy things with some degree of tactical savvy, which I can only assume is the whole reason someone would ask for advice in the first place.
My general advice to beginners of all kinds: spend more time studying the hobby, and less time studying the people within it. Absorb facts, infer from facts, donāt absorb opinion pieces like so many people have been doing this last year especially. Smart people can still give bad advice, people without vested interests can still be misinformed and ignorance is even more common than vested interests.
Studying Pokemon is like studying everything else: you spend more time sieving out misinformation than learning true knowledge, and everyone has an agenda. A rugged sense of individualism will see you through all that. If thatās not an option, try to make friends who will be honest and helpful to you. You can do both, but you need to do at least one.
Personally: I had one rule when I bought big back in the day: never buy unlimited if a 1st edition version exists (except Base set). I didnāt really carethat much about the 1st edition stamp, but I knew the financial implications it would have. And so I only bought 1st ed, a move Iām very pleased with today.
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This may feel backwards, but I would actually join smpratteās patreon and watch all the videos from the beginning to the present. The one month that I took to watch them like it was college lectures introduced me to new sets, nuances within specific sets, market sentiment and cycles, and how to evaluate value of cards that I would like to possibly add to my collection. While it can be nice to go to bulbapedia as well, people in the comments for the Q/Aās ask interesting questions that many of which I wouldnāt have thought of so its like we all learn/discuss together.
I think doing that will help narrow your focus.
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From an investment perspective I would suggest looking at sets pre Black and White and deciding what you like and go from there. I would then consider looking at CGC 9.5ās since very often they would cross to a PSA 10. I also personally think vintage PSA 9ās are undervalued and will eventually have a resurgence in growth and value. However, if you like modern, hey collect that, and yes if you hold it long enough even modern will have its day in the sunshine. Also Japanese promoās have thus far been an excellent investment. At the end of the day the best advice is really just to collect what you enjoy most.
While these suggestions may be great, Iām afraid OP hasnāt logged in ever since the day he posted lol.
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I would start with buying as many Pikachu Illustrator cards as you can whilst also looking out for the complete set of Pikachu Trophy cards. After collecting these you could focus on the sets of Pokemon Snap cards with the occasional Masterās Scroll promo card thrown in. Go with a splash of Tropical Mega Battles and if you have a few pennies left over, splurge on a lovely Family event Kangaskan, beautiful card in my opinion. Of course all these have to be a minimum PSA 10. Once you have collected these you could think about buying Nintendo and start printing your own cards to sell and start recouping a little of your outlay. Then for a real challenge start collecting every card that contains the letter āAā on it.
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I would just buy what you like. If you collected as a kid and have some sort of nostalgia for certain cards or specific PokĆ©mon, then start there. If you donāt really have any sort of attachment to anything, then honestly just buying whatever current set is out is perfect. There are so many cards out there that its really impossible to advise you on what to buy, given that everyone has different preferences. As far as learning about the generations of the cards, that will take much more time to do. There are so many unique cards and sets that it takes people years to really capture it all in, and even then they still learn new things. I wouldnāt focus much, if at all, on the long term investment aspect if you are just entering/returning to card collecting. Its much more fun to just have fun opening packs or picking up some singles here and there. Thatās what I would do.
Some places to start out when expanding your collection:
- Collect a particular artist. Many artists have been around since the very beginning of the tcg
- Buy cards from the era you first started in. If you have attachments to Lv. X cards, buy Lv. X cards! If you remember opening base set, then buy some base set!
- Browse tcgplayer, ebay, and trollandtoad for cards. You can learn a ton about what cards are out there just by searching up a single pokemon.
- Search up a your favorite pokemon and buy some cards that feature it
- Watch people open up packs on YouTube or Twitch. This is both entertaining and quite informative. Itās cool watching someone open a $20,000 booster box or a $20 tin.
- Open whatever set is the newest or whatever you can find in the stores.
I got back into Pokemon last year (after a decade long hiatus) too. Like everyone else is saying: go collect what you like. There are better to invest if you want to maximize return (non traditional assets like Pokemon come with a world of headache if your sole purpose is to maximize return).
Thereās so much out there ā¦ pick a theme and run with it instead of trying to complete multiple collections (or everything under the sun).
I think graded holos are nice. Why not pull the trigger on a zard?