After spending nearly 2 hours and 45 minutes on the phone with Xbox Support, I've submitted the info to try and get about 20 of my old gamertags back. Including 2 letters (Letter Letter) which are unspaced, A 2 character (Number Letter) which is also unspaced, Actual OG Gamertags which are unspaced, as well as a few very nice spaced tags. The only reason I'm able to hopefully get these back is because I still have the console ID these tags were created on 3 years ago.
The only issue that I'm kind of worried about, is the xbox support guy told me (After spending 3 hours on the phone with him), that they only have records of up to a year ago. But I'm hoping that's just with his level of employee, and that his supervisors/the investigation team that he passed the info off to can see farther than that.
I'll start hearing back in 5-7 business days.