...but first I then have to Terminate his employment as COO, which will make him dislike me and won't take employment with me again. :( Why cannot I choose to hire him directly from his COO position? I would transfer all the business assets from my holding company so he could be managing the company...

I think it should be easier to transfer techs, but I don't think it should be for free for the same reason other transfers should not be free (helps to prevent potential manipulation). Agree 100%. Make all assets transferable, not only Firms. Ideally, R&D expense in any entity should be capital...