FYI, the issue with upgrading to Catalina or later is NOT that Carslina and later will run 64-bit applications, and High Sierra won’t.
High Sierra will run both 32-bit and 64-bit applications (though it is too old to run current ones). Catalina and later will only run 64-bit applications. So all of your 32-bit applications break, and you have to find 64-bit replacements / upgrades or go without.
This is especially likely to affect games, as game developers often throw their software over the wall )do to speak), collect money, then move on to the next game without updating the old ones to remain compatible with new platforms.
If you have a lot of 32-bit applications that don’t have upgrade paths, you may want to keep an old machine around just to run them. But at some point, you have to “rip the bandage off” and make the 64-bit-only switch on your main machine so you can use recent Macs and recent versions of macOS.