You have two options when selecting random milestones and awards: Limited Synergy and Full Random.

Full Random is just a mechanism to randomly select milestones and awards, like picking them out of a hat. Nothing interesting there.

Limited synergy is a mechanism where every milestone and award is compared to every other milestone and award, and given a rating from 0-9.

Current version can be seen at https://docs.google.com/spreadsheets/d/1edlOzMbM67MnXRIgFxo4sJ0mSNKkb7pRhK9Tgev9Ueo