For what it's worth, here's a few different responses:
One answer is keeping up to date with changes to Microsoft Windows... for example HighDPI support. Does your software work well with Windows 10 high dpi systems? Delphi is getting much better with this particular issue. Hopefully 10.4 finally fixes some of the issues with VCL Styles and High DPI.
Another answer is compliance related - some compliance certifications require your tooling be kept up to date with all available patches/updates. If you aren't under third party audits, this is less of an issue but for security in general keeping current is wise. (Do you have the buffer overflow fix for Delphi in place?)
Another answer is business risk / insurance related - It may bite you later on any future insurance claims that you knew you were out of date but didn't upgrade to fix any potential problems.
Are you going to milk this thing as it is until it dies, or are you ever going to add new features? If you are going to add features, staying current may make future features easier, especially keeping up with fast changing technologies like AWS/Azure.
If you are using any third party components, eventually they will drop support for older versions of Delphi. You have to assume most of the new activity in third party components surround the new releases. With more and more new language features becoming available (like inline variables) that devs really like to use which aren't backwards compatible, the rate of third party components dropping support for old versions will probably increase over the next few years. This is obviously one of the prime goals of Embarcadero - and they will keep hammering at. It's in their best interest to introduce new non-backwards compatible language features and this approach will succeed over time.
Finally, the longer you wait, the harder it becomes to ever bring it back up to date. It's just delaying the cost today for higher costs tomorrow. If they are in it for the long term, they should act like it.
If you are a one or two-man shop then it's certainly much harder to justify the ongoing costs due to the ever increasing price (which I assume will keep getting worse), but if you are making a decent living with the Delphi products then it only makes sense to keep them current.