It's not really that cryptic. The rollbacks are listed chronologically. The oldest ones are on the top, the most recent ones are at the bottom. FWIW there is no preference for selecting reverse chronological order. The first update is listed first, the second update second, etc.
You're confused because in 2015, updates were named after towns in Boston, in alphabetical order (e.g., Allston preceded Braintree).
As to the numeric ones, 2016.03 precedes 2016.04, which precedes 2016.05, which precedes 2016.06, etc. etc. Based on your screen shot, the most recent update you can roll back to is the last one listed (2016.07).
Also you might want to give some details on your "major, urgent, life-stopping software-failure" because there might be a simple solution.