Upgrading when space seems low: stop app, then cleanup, then rebuild app?

I’m surprised by “disk space is so tight” in my situation. I run cleanup, I have 7.9 GB free, then I run ./launcher rebuild app and it refuses to finish. Is 7.9 GB free when I want to rebuild the app really so little?!

(UPDATE: Now I understand how this can happen. I leave this here for Innocent Bystanders to find in a web search. Please read this entire thread, folks!)