1

One reason I don't like using the configuration section is that it makes debugging much much harder.

debugging ? please explain how it relates to the configuration, and presentation (i.e. preview)
2.
Yes in theory, but in your case it will not change things, unless these "configurations" are copied on any Task (which is just storage, otherwise no real harm)
3.
I was thinking "zip" file that the Task creates and uploads, and a new configuration type, say "external/zip" , and in the config section have something like
url: target: ./wdyt?