What a lovely thread. Been so nice reading everyone's posts here- this is what collecting should be about- bringing joy to people, whether you're a kid, or just a kid at heart.
A lot of my collections have somewhat bittersweet, if not outright sad, memories attached to them, but I've always done my best to keep the silver linings in mind. My direct family has always been into collecting things, but I'm definitely the "nerd" of the family, so a lot of things I got from other family members or friends as a kid were shots in the dark- some of them pretty spot-on, some of them not, but still- because my direct family's financial stability fluctuated growing up, most of what I had were from others, and they were all special to me. A couple examples off the top of my head:
For my 5th birthday, my Mom made me a Batman cake that had the little Batman & Robin MicroVerse vehicles on it, and I thought it was just the coolest thing. My Dad gave her shit for how the cake decoration looked, but I loved it. It was the only time anyone ever made me a cake (my mom never did again- because of what happened, I'm sure), but because of the one-time thing and the fact she got such hate for it, I frickin' love those little vehicles, even to this day. I used to carry around the Bathammer in my pocket in elementary school as a little reminder to stay brave, and even now, just looking at them brings me joy because of how much love went into putting them on the cake.
I know I've mentioned it a few times as well, but my Dad being the, shall we say, "complicated" man he was, there were very few things that humanized him or allowed us to bond, but every so often there'd be a fleeting moment where his inner kid would shine through. Despite his best attempts to get me to like a lot of the same things he did, I just never clicked, except on one franchise- Star Wars. We watched the movies together a bunch, talked theories on where the next movie would go, talked about our favorite characters, and he'd even let me play with the Micro Machines playsets, which were some of his most prized possessions. I looked forward to the prequels because it meant that my father and I would actually get to act like father and son again. Most of my toys I'd have to do things for- either chores or less savory things we won't get into, but Star Wars was again the exception. I'll never forget for the ROTS line, he'd call the house on his way home from work, rifle through the pegs and ask me who I wanted/needed. Never let me have the female characters, of course, but he seemed more than happy to get me anyone else I wanted. I've obviously updated a bunch of them through the Black Series, but a bunch I've kept, just because through them, I can still feel oddly close to my Dad.
On a similar note, toward the end of the line, when, at least in my area, the figures became less plentiful and harder to get, I was spending the day with my uncle (Dad's brother), who was also a huge SW fan, and he bought me the Anakin where you could swap between the hooded look or his crispy Mustafar look. I ended up getting in big trouble for it- not only for letting someone else buy me something, but I'm sure my Dad's ego took a blow from someone else sharing SW with his son. But still, I love that figure even now because that was maybe the only time I ever went shopping and got to nerd out with my uncle.
After my parents separated and we were barely scraping by, toys became basically non-existent. In fact, I had to sell most of my old ones to make ends meet. But every so often, my Mom would surprise me with a new toy while picking me up from school- she knew how hard things were and had been for my sister and I, and would try and cheer us up now and then. She worked at Target and if something came in damaged, her manager would basically just turn away and let her have it- not that I condone stealing, but it's the only way she was able to give us as normal a life as possible. That's how I got the Leader Class Megatron from the 07 movie, which to a wellfare kid like me was, like, the coolest thing ever. Also got a bunch of Pirates of the Caribbean figures that way, which I still display. Dead Man's Chest was the last movie we saw together as a whole family, and At World's End was the first we saw after the divorce, but also the last movie we saw in theaters for years because we just couldn't afford it, so getting those figures was, and still are, really meaningful for me.
Last one I can think of is a bit silly, but it's the recent Jakks Pacific Simpsons line. We used to watch the Simpsons all the time growing up, one of the few shows we watched as a family. The only toys we ever saw were either super side characters I didn't care for, or the church versions of the Simpsons themselves. Even as a kid I didn't really care for variants or alternate looks- I just wanted the plain, basic looks for each character, especially Bart. For whatever reason, my Dad like obsessed over finding just the basic Homer figure. It was his white whale. He never did, though, and he's since passed. I know it's not the original figure he wanted, but getting the Jakks Homer and Bart really gave me an odd sense of closure. Every time I see the old Playmates Homer in a secondhand shop, I always get hit with a little pang of some kind of Happy Sadness.
I think that's why I still love collecting now- it not only allows me to have the things I wanted as a kid or had to sell, but it also brings me back to these bittersweet, yet ultimately happy, memories I have of some of my now departed loved ones. Funny, how it all works- life, grief, closure, happiness. I know all this may seem pretty sad or desperate on the outside, but I promise it all brings me (mostly) joy nowadays.