I recently found out that archive.com, besides being generally amazing, has exhaustive collections of content. This includes files for pretty much every videogame ever released, up to Wii/PS3 era and some beyond.
Obviously these things are being updated, but the missing content is limited to stuff like 'Flemish Beta release'. If that sounds appealing to you, then we share an illness. There are also curated collections out there (eg Champions collection) if you don't want to sift through all that toss.
I found out that emulation has evolved a bit since my day, and now you have the option of consolidating emulators within a frontend, like Retroarch - https://www.retroarch.com/index.php
There are a bevy of handheld or plugin consoles that can emulate some fairly modern systems. There's also Retropie and stuff like that, so you can basically create your own emulation platforms. It's mental what's gone on since I last looked in.
On the obsessive side, there are numerous groups (ReDump, No Intro, 1G1R, TOSEC) who create their own 'dat' files, which contain all expected files and can be used to verify a checksum to validate the rom file. There's rom management software, like the picture attached - I've recently found that it's easy to create your own dat files using clrmamepro (rom management focused on MAME, the arcade emulator), so I'm now sorting my collections into a few groups so I can host the core ones on an ftp for when my HDD inevitably dies.
Finally, if you duckduckgo (no wonder they aren't taking off, how the fuck do you shorthand that?) 'games over girls' you'll find a slightly disturbing set of photos of women dressed up as game characters and feigning unconsciousness in awkward poses.
I've got a folder that I have transferred off an old USB stick onto any fresh computer build/installation I've made over the last fifteen years or so. It contains portable copies of Doom and Quake with a shitload of wads, and emulators with a full set of roms for every 8 and 16 bit console. Can't have a computer without the basics.
>>24778 WinAmp was a Matryoshka doll of constrained creativity. You highlighted skins, but there were several visualisation plugins which had their own plugin or configuration language (I didn't learn about cartesian v.s. polar coordinates this way, but I first understood how the latter work way back).
I wonder some times if its rose tinted memories (the demo scene is obviously alive and well), but even the ways you get started with modern technology feel like a hand-holding exercise. The step towards "learn to code" is so much easier, but the step towards "actually learn to code" is harder.