Ok, so I did some more tests on this.
The only way I was able to call multiple CSS was by using a StyleSheetExtension with the imports inside of it:
@import "$services.webjars.url('org.webjars:font-awesome', 'css/fontawesome.min.css')";
@import "$services.webjars.url('org.webjars:font-awesome', 'css/solid.min.css')";
@import "$services.webjars.url('org.webjars:font-awesome', 'css/regular.min.css')";
@import "$services.webjars.url('org.webjars:font-awesome', 'css/v4-shims.min.css')"
Using xwiki.iconset.css ended up loading just the last declared value (v4-shims.min.css)
xwiki.iconset.css = $services.webjars.url('org.webjars:font-awesome', 'css/fontawesome.min.css')
xwiki.iconset.css = $services.webjars.url('org.webjars:font-awesome', 'css/solid.min.css')
xwiki.iconset.css = $services.webjars.url('org.webjars:font-awesome', 'css/regular.min.css')
xwiki.iconset.css = $services.webjars.url('org.webjars:font-awesome', 'css/v4-shims.min.css')
Now, if there is no problem using the StyleSheetExtension then it would work ok.
On jstree we can just update the references on tree.less
to the new unicode values (there are only 3 icons). It is a mitigation only but would work in the short term.