Would it be best to try and earn an associates degree while attending AIT or wait until after AIT graduation?

Your number one priority during AIT is to become technically proficient in your MOS. At most, I’d recommend work towards maxing your correspondence courses. Otherwise just focus on learning you job, you’ll have plenty of time at your first duty station and the rest of your career to take care of college.

You won't have time. Trust me.

Additionally, benefits like TA can not be used until you get to your first duty station. So even if you were to attempt to do college courses while in AIT, it would be out of pocket.