Yes. Upgrading really old php application (v4? really?) to v8 is such a big step it will need much dedication, so many things changed between 4 and 5 its not easy. And even upgrading 5 to 7 may break so many things. I would not like to switch with him.
> Adding tests for an app with no documentation requires a lot of effort.
code tests yes. Assuming it's a web app, probably not too hard. Get something that records the browser interactions, and do the common tasks people do (log in, click links, make a report, etc). Having general things like that automated to ensure you can run them repeatedly to make sure basic stuff didn't break unexpectedly will help provide some confidence when making changes.
Adding tests for an app with no documentation requires a lot of effort.