People who grow up using these sorts of bespoke software are gonna have some pretty weird nostalgia. "Hey when you were a toddler did you ever play with a paint app where the fill tool created flashing swirly patterns? ...no?"
I have a friend who's dad is a good carpenter, put a whole second story on his house, did the flooring and made a lot of furniture. He said it was about 4th grade before he found out that there were stores where people went and bought furniture instead of just making their own.
My parents aren't especially skilled carpenters, electricians plumbers, or HVAC technicians, but they managed to be good enough at those things. At sixteen my girlfriend's family was flabbergasted to learn that I had never seen my parents hire such people.
My dad was also a pirate, and I had a similar experience when I learned that you could buy VHS tapes with pictures of the lion king on them, rather than just "Lion King" in dad's handwriting.
He did not wear an eyepatch or kill people, he did sail the high seas on occasion, he recorded both TV and made vhs and cassette tape copies, I don't think he ever sold these copies.
Though I'd like to propose that it's actually about exploring prohibited alternatives in spite of a failing authority, which is why the "of the caribbean" era pirates were democracy enthusiasts.
Reminds me of the Nanny Lynn tapes that everyone was wondering what the hell it was about for a while like it was some kind of analogue horror thing and then it turned out to be just some cartoon someone made for their grandkids or something
On the subject of nostalgic paint apps, I distinctly remember one of the Kid Pix drawing tools/games that I had growing up... what a weird piece of software that was!
That makes a whole three of us. I played it on NES, and it wasn't until I was in my 20s I learned to it existed on other platforms too. My dad and I spent days on that game trying to figure out good strategies and how to beat it. Good memories.
I think we're well past the point where anyone is feeling that level of nostalgia for software.
Unless they are explicitly reminded (immediately ruining any sentiment other than indifference), they're more likely to find closure mistaking it for something else.
We just saw this play out over the last 20 years with meme pollution.