This article was quite useful. I am actually running into this trap more often than not lately.

Links and comments here have been greatly helpful. I do not know if a solution for this issue will be added to the core anytime soon. However an easier solution to this dependency management hell could be to pay closer attention to how the ClassLoader gets implemented.

Yes it is not ideal to add our dependencies to the plugin package, however since there's no better availability do date this is a necessary evil.