Any form of IBD is disqualifying and very difficult to get a waiver. Having no symptoms for years is a good thing. MEPS will ask for evaluations from a gastroenterologist. Treatment records, medications used, etc. I think for OCS, it is very unlikely to get a waiver.
We have a saying in the Army: "Right time, right place, right uniform." Literally do those things and you are good. Evidently, there is a failure to do all of these things. Not just once but several times. This is something I might expect from a junior enlisted SM, not a potential officer.
Efficient means having the highest probability of achieving your goal with the least time required. It's been said many times over on this forum that going to medical school, or any other medical profession for that matter, is one of the least likely to be achieved through a Service Academy or ROTC.
The expiration date is the longest that a manufacturer can guarantee stability under ideal conditions. Beyond that, the medication is still "good" but the chemical structure begins to break down and lose its effectiveness. There are some studies out there showing how effective a medication is...
While I find that also unacceptable.. at least a Presidential Inauguration is for an active form of government and not an egregious display of vanity on the part of the "royal family."