I agree with how Flamestrike resolves combat except regarding the Assassinate ability.
The Assassiante ability states (emphasis mine):
PHB said:
Starting at 3rd level, you are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.
In the mentioned example, since the guard had a turn, I wouldn't let the rogue get advantage from Assassinate, but I would let him get the auto-crit due to successful surprise.
So breaking the scenario into a step-by-step process I would rule it as:
1. Rogue successfully sneaks into position behind bushes (winning the Stealth vs Passive Perception contest)
2. Rogue declares he wants to attack the guard from behind the bushes -> this begins combat sequence
3. Initiative is rolled - Guard wins initiative
4. Round 1: Guard is surprised so he can't move or take actions
5. Round 1: Rogue attacks guard with advantage. Since guard already had a turn, Assassinate (advantage) doesn't trigger, but Assasinate (crit) does, due to him being surprised. However since rogue is hidden until his position is revealed, he has advantage from being unseen. Guard now has reactions available so he could cast the
Shield spell if he, for some reason, knew it.
6. Round 2: Guard, if still alive, gets to act normally. Continue standard combat