Here's a real example of that bug:
Slack's message buttons (such as "Add reaction" or "Reply in thread") stopped working for Firefox versions >= 100 and <= 519. They mysteriously started working again for versions >= 520. The version string "100" compared as smaller than "52" in Slack's code, which activated some kind of webcompat workaround intended for Firefox versions < 52 that breaks on more recent Firefox versions.
I also fear there’s software that correctly extracts all the digits of the version in the user agent, but then compares it as a string with a given version. That would get you