Should everyone have at least an Associates Degree upon retiring from the military?

No... people should have a degree if they want a degree. Sure there are plenty of resources to utilize to get an education, but what if you don't want an education. I've seen people going to college and they purposefully sign up for the easiest classes so they get high grades in subjects they don't care about and essentially learn nothing.

Some people also might not want a career in anything that requires a degree, so they might opt to go to a trade school instead and get a certificate.

Believe me, I love learning and I think education is it's own reward, but I don't expect everyone to have that same passion for knowledge.

I think everyone should at least have a bachelors or have a plan to obtain a bachelors upon ETS.

yes they should..
And Yes, the Services SHOULD be hiring accredited professors to teach professional military education for enlisted SM. So that when said and done, they have many credits to complete a degree.
Instead we "save money" by assigning military members to teach our own..Mil members that have only most basic training in being an educator (couple of hours in a classroom at best, and then some left seat./ right seat time with an outgoing instructor if lucky) and many times are only educated enough them selfs to hand out POI approved tests, and "correct" a multiple choice answer sheets.

I have the 1059's, NCOERs, award recommendations ect that PROVE only one out of a dozen are capable them selfs at having a chance in assigning and reviewing a written assignment.

With writing now being a components of NCOES, I struggle to understand who and how NCOES school instructors are reviewing and grading these papers tuned in.