I think that would be great to be able to add a file, or even several files, directly to my wingman UI to ask him to analyze it, using skills. Either with a "browse" button or a drag'n drop (both would be awesome). That would be much easier than having to setup a skill for a given directory.

I do that in perplexity, I ask perplexity to analyze a pdf or word contract, to check errors or to propose better ways to write that.