Widget Template Issues

[The Honor Empire]

Some background first: I created a copy of the Recent Images gallery Widget using the plugin format for templates and css. It works in dev mode, but not in "live" mode. So, I downloaded the widget, deleted the existing copy, and uploaded it out of dev mode. It works in live mode now. So there must be some database trickery in the background for installing the widget into the system outside of dev mode.

The Issue: When I go into dev mode, after uploading the XML copy I downloaded earlier and then uninstalled, my widget doesn't have the template file anymore. The CSS and PHTML files are not created on the disk. So the moment you go into DEV mode with a widget, it'll stop working as those templates and css files are not recreated on disk.

I can re-upload the phtml and css files to get the widget working again. However, why is it not creating the phtml and css files when going into developer mode? Is this a bug?