I think artificially breaking the existing loaded file would be a mistake. What if you're working on a core service that *must* execute in order to view any (and all) page? You've just broken the entire site! You can't use the UI to troubleshoot or adjust settings...bad idea.
An alternative to breaking the package would be to flag the package file's reload status on the APM's watch/status page. Maybe even catch and display the result of the reload (error messages) on an APM page.
Maybe a red X icon next to the package/file that, when clicked, would display the error report?
