I’m personally never going to sell my main collections. Pikachus, Sevipers, FA Supporters, Moltres #21 promo variations, and National Index. These collections will be with me for the rest of my life. I might stop collecting some of them, like I did with my Mimikyu collection, but I’m not gonna sell them. I’ve once threw away my pogs/flippos collection, and even though I hadn’t looked at it in over 10 years, I still kinda regret it because it would be fun to look back at it once more and have the nostalgic memories kick in. And that’s with a collection I wasn’t really engaged in at all.
For Pokémon it’s the complete opposite. Currently collecting Pokémon cards is a part of my life, and even if I stop collecting when I get married / have kids, or maybe in the much more distant future grandchildren, I won’t ever sell my collection. I might downside the rest of my Pokémon cards, but these mentioned above. Nope, never.
I also don’t think I’ll ever be in a financial difficult state where I would be forced to sell stuff in order to survive tbh. If I get in a financially difficult state I might not be able to chase Pokémon cards (Pikachus in particular) like I do now, considering how rapidly new Pikachus are getting released and how expensive some of the cards are I still need. But I honestly don’t think I’d ever need to sell my collection. I have a good job as software developer, and would be able to find a new job within a week at the moment. Also, here in The Netherlands you are helped by the government if you have are ill or had an accident and can’t work anymore.
So, having said all that, I hope to one day pass them onto my children or grandchildren. When I was 6 years old my very first collections were post stamps and pretty peddles/rocks. Later on my mom gave me her post stamp collection when we moved and we came across her collection in the attic. And later my uncle and grandma gave me their post stamp collections as well. Admittedly, I haven’t collect post stamps much the past decade, except for the Chrismtas set every year, but it’s still cool to have a collection spanning three generations. I don’t even know how much post stamps are worth tbh, and talking about this now makes me wonder if there are some hidden gems in this collection. But, it’s cool to have this collection span multiple generations, and I hope the Pokémon TCG will continue and continue, so in 50-60 years from now we can all also say the same with our Pokémon collections spanning multiple generations (except for @garyis2000 probably, since I don’t think he’ll survive another 60 years, haha rip buddy ).
I hope to pass some on but sell others. My modest profession is as a physics teacher and a life goal is to retire a millionaire by making smart investments. That includes Pokémon, but certain cards will hold significant value through trades, gifts or pulls. I hope to be in a position to decide as I please when the time comes but I just want to pass on my enthusiasm and display my collection proudly.
I have an interesting (sometimes sad) perspective on this from my involvement with breweriana collectibles. That collector base is generally a fair bit older and sadly passing away with very few new young collectors moving into it.
I’ve bought multiple collections from widows and children that steins were passed onto or left behind with. People who generally just have no interest in them and see them as somewhat of a burden either figuring out how to sell them or lugging them around with them. Burden also manifests as guilt sometimes not wanting to get rid of them but not having the finances or space to keep them. Many have no idea of their current value but a good idea of the money that went into the collections. Some have records that their late family members kept as they assembled the collections. Sadly most of these values dropped across the board which makes it even harder telling them the items are worth only a fraction of what their loved one put in. Obviously as of recent Pokemon hasn’t had that unfortunate happening but in 20-50 years time who knows.
I never want to leave anyone in that scenario. I try to keep good records and organization of what I have and I’ve recently tried to work on selling through or at least listing a lot of my backlog.overflow/things that don’t fit my collection. I envision myself downsizing or at least not materially expanding very much what I have in 10-20 or so years time. Unless my kids take interest in it and I can use it as a way to bond and spend time with them (hopefully that is the case). If I do plan to leave anything behind I definitely want it to be liquid and smaller in size and quantity than I have currently so that it isn’t too burdensome whether anyone after me decides to keep it or sell it off.
We’ll see where the winding road of life takes me.
My last will and testament must include a clause that states that my collection should be cremated together with my body.
Then, a few minutes into the service, when the chamber is locked and merrily burning away, a pre-recorded video starts to play on the chapel’s tv for everyone to see. After I say my goodbyes in the video, I start to read a list of some note-worthy cards in the collection, while some IT guy pulls up ebay recent sold listings and merges the feed with the video. (Note that at this point, these cards will be 60+ years old). As people start panicking and crying over the lost value of said cards, my sister (8 years younger than me) starts to remember what I always say when she asks how my collection is going along, to which I usually reply with “My pack pulls are lit!” or “My collection is on fire!”; and as the realization of this decades-old running joke dawns on her, a grim smile spreads across her wrinkled face as she whispers to herself: “Well-played, brother.”
Only then can I truly rest in peace, knowing that I have one-upped my sibling one last time.
But, it’s cool to have this collection span multiple generations, and I hope the Pokémon TCG will continue and continue, so in 50-60 years from now we can all also say the same with our Pokémon collections spanning multiple generations (except for @garyis2000 probably, since I don’t think he’ll survive another 60 years, haha 
rip buddy 
).