In answer to OP:
3. Confirmed, V5e8: https://youtu.be/vi8y8PxW5h4?t=8m40s
5. I could come to ship it...
8. Oscar is the most precious cinnamon roll ever and I will personally feed anyone who hurts him to a Beowulf
Also, a theory-ish thing:
I assume that Professor Ozpin was not the first body the Wizard had. If that's true, then how come we never see Ozpin "transform" into one of his former personas? Furthermore, if there were people before Ozpin, how come Oscar doesn't transform into one of them?
One answer is that the current Wizard will absorb the old form's memories and skills, and otherwise develop as they normally would. In that case Ozpin would essentially be dead for good. Another option is that the ORIGINAL Wizard has been continually taking over new hosts this whole time, and Oscar will permanently let Ozpin have control while sitting passively in the background for the rest of his life. A third possibility is that their personalities will join: Ozpin will become like the normal voices we all hear in our heads, giving us the advice our parents used to give us or whatever. It could totally be something I haven't thought of yet, so tell me your ideas! I just really hope it isn't Option 2.
(Oh, also also: How will Ozpin and Oscar's semblances work now?)