Hi. New to these boards, but I've learned how to rules-lawyer from some of the best, so I hope you're willing to hear me out.
I'm not really feeling willing to read up on most of this, but I may be able to help with this tricky "Awaken" loop we're dealing with. Cracking out my handy SRD, I'm looking at the "Target" line of the spell description. It specifically mentions the term "animal", as does the spell text. "Animal" is defined as a creature type, which is mentioned in various locations to be unable to have an intelligence higher than 2. Therefore, any creature or character with an intelligence of 3 or higher is an illegal target for the Awaken spell. Since the target of the spell has 3d6 intelligence, they can't be an animal (due to a minimum of 3 intelligence from the roll), and therefore becomes an illegal target for the spell. No DM finesse, no crazy cross-examples. As written, the Awaken spell can be used on a target animal once and only once. Now, if you could turn yourself into a tree, you'd have something, but I have yet to see a spell that allows that.